Buy (4ANPP) Depropionylfentanyl CAS 21409-26-7

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1-(b-Phenethyl)-4-anilinopiperidine

Purity: >95%
Catalogue #: DC-001214
CAS #: 21409-26-7
Availability: In Stock
Molecular Formula:C19H24N2

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Buy (4ANPP) Depropionylfentanyl CAS 21409-26-7

Buy (4ANPP) Depropionylfentanyl CAS 21409-26-7

CAS 21409-26-7

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4-Anilino-N-phenethylpiperidine (ANPP)

Description:

4-Anilino-N-phenethylpiperidine (ANPP) is a synthetic chemical compound primarily recognized for its role as an intermediate in the synthesis of various psychoactive substances, particularly fentanyl analogs. It features a piperidine ring, which is a six-membered nitrogen-containing heterocycle, and is substituted with an aniline group and a phenethyl moiety. ANPP is characterized by its relatively complex structure, which contributes to its pharmacological properties. The compound is typically a white to off-white crystalline solid and is soluble in organic solvents. Due to its structural similarity to other opioids, ANPP exhibits affinity for opioid receptors, which can lead to significant analgesic effects. However, it is also associated with potential for abuse and dependence, necessitating careful regulation. The compound is not widely used in clinical settings but is of interest in research and forensic contexts. As with many synthetic opioids, safety and handling precautions are essential due to its potency and the risks associated with opioid exposure.

Formula:C19H24N2
InChI:InChI=1S/C19H24N2/c1-3-7-17(8-4-1)11-14-21-15-12-19(13-16-21)20-18-9-5-2-6-10-18/h1-10,19-20H,11-16H2
InChI key:InChIKey=ZCMDXDQUYIWEKB-UHFFFAOYSA-N
SMILES:N(C1CCN(CCC2=CC=CC=C2)CC1)C3=CC=CC=C3

Synonyms:

  • 1-(2-Phenylethyl)-4-phenylaminopiperidine
  • 1-Phenethyl-N-phenylpiperidin-4-amine
  • 4-Anilino-1-(2-phenethyl)piperidine
  • 4-Anilino-1-(β-phenethyl)piperidine
  • 4-Anilino-1-phenethylpiperidine
  • 4-Piperidinamine, N-phenyl-1-(2-phenylethyl)-
  • 4-anilino-N-fenetilpiperidina (ANPP)
  • 4Anpp
  • ANPP, N-phenyl-1-(2-phenylethyl)piperidin-4-amine
  • Depropionylfentanyl

4-ANPP, also known as 4-anilino-N-phenethylpiperidine (4-ANPP), 4-aminophenyl-1-phenethylpiperidine, or despropionyl fentanyl,[3] is a direct precursor to fentanyl and acetylfentanyl. It is commonly found as a contaminant in samples of drugs containing fentanyl, which may include samples represented by the supplier as heroin or other opioids.[4] It is not psychoactive and is present only as a result of improper chemical purification.

4-ANPP is useful in the synthesis of pharmaceuticals, primarily fentanyl and related analogs. Paul Janssen (founder of Janssen Pharmaceutica) first synthesized fentanyl in 1960 using a similar method, with Benzylfentanyl as an intermediate.[5] The following synthesis, developed by an individual under the pseudonym of Siegfried, involves the reductive amination of N–phenethyl-4-piperidinone (NPP) with aniline to make to 4-ANPP. This product is reacted with propionyl chloride or acetyl chloride to form either fentanyl or acetylfentanyl.

See also

1-phenethyl-N-phenylpiperidin-4-amine

Cat. No.:B3395214
CAS No.:21409-26-7
M. Wt:280.4 g/mol
InChI Key:ZCMDXDQUYIWEKB-UHFFFAOYSA-N
Attention:For research use only. Not for human or veterinary use.
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Description

 

1-Phenethyl-N-phenylpiperidin-4-amine, more commonly known as 4-ANPP or Despropionylfentanyl, is a compound of the 4-anilidopiperidine class, which is a well-established pharmacophore in medicinal chemistry . This scaffold is the structural foundation for a family of potent synthetic opioid analgesics, most notably fentanyl . The primary research application of 4-ANPP is as a key synthetic intermediate and precursor in the study and chemical synthesis of fentanyl and its numerous analogues . It is a direct intermediate in the “Siegfried method,” a known synthetic route to fentanyl . Researchers value this compound for investigating structure-activity relationships (SAR) within the 4-anilidopiperidine series, as modifications to the core structure can significantly alter biological and pharmacological activities . Due to its role in the synthesis of controlled substances, 4-ANPP is recognized as a controlled substance precursor and is subject to regulatory controls in multiple jurisdictions, including being listed as a Category 1 substance in the European Union . This product is intended for forensic analysis and chemical research purposes only. It is strictly for laboratory use and is not intended for human or veterinary use. Researchers handling this compound should be aware of and comply with all applicable local, state, and federal regulations.

 

Properties

IUPAC Name

 N-phenyl-1-(2-phenylethyl)piperidin-4-amine

InChI

 InChI=1S/C19H24N2/c1-3-7-17(8-4-1)11-14-21-15-12-19(13-16-21)20-18-9-5-2-6-10-18/h1-10,19-20H,11-16H2

InChI Key

 ZCMDXDQUYIWEKB-UHFFFAOYSA-N

Canonical SMILES

 C1CN(CCC1NC2=CC=CC=C2)CCC3=CC=CC=C3

Molecular Formula

 C19H24N2

DSSTOX Substance ID

 DTXSID40175680

Molecular Weight

 280.4 g/mol

CAS No.

 21409-26-7

Synthetic Methodologies and Chemical Transformations of 1 Phenethyl N Phenylpiperidin 4 Amine

 

Established Synthetic Routes to 1-Phenethyl-N-phenylpiperidin-4-amine

The synthesis of this compound, also known as 4-anilino-N-phenethylpiperidine (ANPP), can be achieved through several established chemical pathways. These routes primarily involve the formation of the core piperidine (B6355638) scaffold and the subsequent introduction of the N-phenethyl and N-phenylamino substituents.

Reductive amination stands out as a prevalent and efficient method for the synthesis of this compound. This approach typically commences with the reaction of N-phenethyl-4-piperidone (NPP) and aniline (B41778). The initial reaction forms an imine or enamine intermediate, which is then reduced in situ to the desired secondary amine.

A common protocol involves the use of sodium triacetoxyborohydride as the reducing agent. This reagent is favored for its mildness and selectivity, allowing for the efficient conversion of the imine to the amine without reducing other functional groups.  The reaction is typically carried out in a suitable solvent, such as dichloromethane or dichloroethane, often in the presence of an acid catalyst like acetic acid to facilitate imine formation.  Alternative reducing agents, such as sodium borohydride, have also been employed.  Another variation of this method involves a one-pot reaction where 4-piperidone is first reductively alkylated with phenylacetaldehyde to form N-phenethyl-4-piperidone, which then undergoes reductive amination with aniline in the same reaction vessel.

Reactants Reducing Agent Solvent Yield (%)
N-phenethyl-4-piperidone, Aniline Sodium triacetoxyborohydride Dichloromethane, Acetic Acid 91
N-phenethyl-4-piperidone, Aniline Sodium borohydride Not specified Not specified
4-Piperidone, Phenylacetaldehyde, Aniline Sodium triacetoxyborohydride Not specified Not specified

This table summarizes common reductive amination protocols for the synthesis of this compound.

An alternative synthetic strategy involves the direct alkylation of N-phenylpiperidin-4-amine with a phenethyl halide, such as 2-(bromoethyl)benzene or 2-phenylethyl chloride. This reaction is typically carried out in the presence of a base to neutralize the hydrogen halide formed during the reaction. The choice of base and solvent can influence the reaction’s efficiency and yield. This method is contingent on the availability of the N-phenylpiperidin-4-amine precursor, which itself can be synthesized from 4-piperidone.

Beyond the direct functionalization of pre-existing piperidine rings, alternative methods focus on the initial construction of the core piperidine scaffold. One notable approach is the Dieckmann condensation.  This intramolecular cyclization of a diester, formed from the reaction of phenethylamine with two equivalents of an acrylate ester (like methyl acrylate), yields a β-ketoester.  Subsequent hydrolysis and decarboxylation of this cyclic product afford N-phenethyl-4-piperidone, a key intermediate that can then be converted to this compound via reductive amination as previously described.

Another approach starts from pyridine derivatives. For instance, 4-anilinopyridine can be acylated and then alkylated with a phenethyl halide to form a pyridinium salt. Subsequent reduction of the pyridine ring yields the desired piperidine structure.

Optimization of Reaction Conditions and Yields

Significant research has been dedicated to optimizing the reaction conditions for the synthesis of this compound to maximize yields and purity. For the widely used reductive amination of N-phenethyl-4-piperidone with aniline, studies have shown that using sodium triacetoxyborohydride in the presence of acetic acid can lead to excellent yields, often exceeding 90%.  The use of cesium carbonate as the base in the alkylation of 4-piperidone with 2-(bromoethyl)benzene has also been reported to provide high yields of the intermediate N-phenethyl-4-piperidone, in the range of 88%.

Synthetic Step Reagents and Conditions Yield (%)
Alkylation of 4-piperidone 2-(bromoethyl)benzene, Cesium carbonate 88
Reductive Amination of NPP Aniline, Sodium triacetoxyborohydride, Acetic acid 91
Acylation to Fentanyl Propionyl chloride, Diisopropylethylamine 95

This table highlights optimized yields for key steps in a common synthetic route to fentanyl, starting from 4-piperidone.

  • N-Phenyl-1-(2-phenylethyl)piperidin-4-amine

    N-Phenyl-1-(2-phenylethyl)piperidin-4-amine

    Controlled Product

    CAS:

  • N-Phenyl-1-(2-phenylethyl)piperidin-4-amine

    N-Phenyl-1-(2-phenylethyl)piperidin-4-amine

    Controlled Product

    CAS:

    Formula:C19H24N2
    Color and Shape:Neat
    Molecular weight:280.41
  • 4-Aminophenyl-1-phenethylpiperidine
    TRC

    + Info

    4-Aminophenyl-1-phenethylpiperidine

    Controlled Product

    CAS:

    Impurity Fentanyl Impurity D / Fentanyl USP Related Compound E
    Applications 4-Aminophenyl-1-phenethylpiperidine is a metabolite of 3H-Fentanyl (F274990), which is used as an analgesic.Controlled Substance.
    References Labroo, R., et al.: Drug Metab., Disposition, 25, 1072 (1997); Zernig, G., et al.: Life Sci., 57, 2113 (1995); Bot, G., et al.: J. Pharmacol. Exper. Therap., 285, 1207 (1998);

    Formula:C19H24N2
    Color and Shape:Neat
    Molecular weight:280.41
  • 4-ANPP

    4-ANPP

    Controlled Product

    CAS:

    4-ANPP is a solution in acetonitrile that is commonly used in the production of biodiesel. It is also used as an intermediate for the synthesis of various compounds, including β-ionone and hydroxyapatite. 4-ANPP has been shown to have controlled release properties, making it suitable for use in controlled-release products. It can be used as a phosphatase inhibitor, preventing the breakdown of phosphates in biological systems. Additionally, 4-ANPP has been found to enhance biomass production and improve cell growth in certain applications. Its unique properties make it a versatile compound for various industries, including pharmaceuticals, agriculture, and research.

    Formula:C19H24N2
    Purity:Min. 95%
    Color and Shape:Powder
    Molecular weight:280.41 g/mol

    Ref: 3D-IP17824

    1mg

    179.00€

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  • 4-Aminophenyl-1-phenethylpiperidine (Fentanyl Impurity) (1mg/ml in Acetonitrile)
    TRC

    + Info

    4-Aminophenyl-1-phenethylpiperidine (Fentanyl Impurity) (1mg/ml in Acetonitrile)

    Controlled Product

    CAS:

    Formula:C19H24N2
    Color and Shape:Colourless
    Molecular weight:280.41

    Ref: TR-KIT2895

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    1,013.00€

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  • CymitQuimica logo

    Fentanyl Related Compound E CII (N-Phenyl-1-(2-phenylethyl)-4-piperidinamine)

    Controlled Product

    CAS:

    4-anilino-n-phenethylpiperidine (anpp)
    Formula:C19H24N2
    Color and Shape:White Light Brown Crystalline Powder
    Molecular weight:280.19395

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    Synonyms Order 4-Anilino-N-phenethylpiperidine (4-ANPP) Precursor
    • 4-Aminophenyl-1-phenethylpiperidine-13C6
    • 4-Anilino-N-phenethylpiperidine-13C6
    • Despropionyl fentanyl-13C6
    Technical Information
    Formal Name: 1-phenethyl-N-(phenyl-13C6)piperidin-4-amine
    CAS Number 2748319-07-3
    Molecular FormulaC13[13C]6H24N2
    Formula Weight286.4
    Purity≥98%
    Formulation(Request formulation change)
    A neat solid
    SMILES
    [13C]1(NC2CCN(CCC3=CC=CC=C3)CC2)=[13CH][13CH]=[13CH][13CH]=[13CH]1
    InChi Code
    InChI=1S/C19H24N2/c1-3-7-17(8-4-1)11-14-21-15-12-19(13-16-21)20-18-9-5-2-6-10-18/h1-10,19-20H,11-16H2/i2+1,5+1,6+1,9+1,10+1,18+1
    InChi Key
    ZCMDXDQUYIWEKB-WGIVQRENSA-N Order 4-Anilino-N-phenethylpiperidine (4-ANPP) Precursor
    Regulatory Information
    DEA Schedule
    II Order 4-Anilino-N-phenethylpiperidine (4-ANPP) Precursor
    Shipping & Storage Information
    Storage-20°C
    Shipping Room Temperature in continental US; may vary elsewhere
    Stability ≥ 73 months

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    1.Pease, J.P., LePine, A.J., and Smith, C.M.Methods for preparing fentanyl and fentanyl intermediatesPatent Application PublicationUS 2013/0281702 A1(2013) 2.Watanabe, S., Vikingsson, S., Roman, M., et al.In vitro and in vivo metabolite identification studies for the new synthetic opioids acetylfentanyl, acrylfentanyl, furanylfentanyl, and 4-fluoro-isobutyrylfentanylAAPS J.19(4)1102-1122(2017) 3.Labroo, R.B., Paine, M.F., Thummel, K.E., et al.Fentanyl metabolism by human hepatic and intestinal cytochrome P450 3A4: Implications for interindividual variability in disposition, efficacy, and drug interactionsDrug Metab. Dispos.25(9)1072-1079(1997) 4.Melent’ev, A.B., Kataev, S.S., and Dvorskaya, O.N.Identification and analytical properties of acetyl fentanyl metabolitesJ. Anal. Chem.70(2)216-224(2015) 5.Steuer, A.E., Williner, E., Staeheli, S.N., et al.Studies on the metabolism of the fentanyl-derived designer drug butyrfentanyl in human in vitro liver preparations and authentic human samples using liquid chromatography-high resolution mass spectrometry (LC-HRMS)Drug Test Anal.9(7)1085-1092(2017)

     

    4-ANPP (Item No. 18810) is an analytical reference material categorized as an opioid metabolite and a precursor in the synthesis of fentanyl (Item Nos. ISO60197 | 22659 | 14719) and other opioids. 1, 2, 3, 4, 5 4-ANPP is a metabolite of acetyl fentanyl (Item Nos. ISO60128 | ISO00128), butyryl fentanyl (Item Nos. 19734 | 14728), furanyl fentanyl (Item Nos. 19633 | 18705), acrylfentanyl (Item Nos. 23060 | 19312), and fentanyl. 1, 2, 3, 4 It has also been found as an impurity in illicit fentanyl preparations. 6 4-ANPP is regulated as a Schedule II compound in the United States.

    4-ANPP (N-phenyl-1- (2-phenylethyl) -4-piperidinamine), a new opioid drug, classified as piperidinamine, synthesized as an intermediate between fentanyl from N-phenethyl-4-piperidone. 4-ANPP is a metabolite of acetylfentanil, butyrylfentanyl, furanylfentanil, acrylfentanyl and fentanyl. 4-ANPP is produced on modern chemical equipment, by professionals who know their business, which makes it clean and of high quality.

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    4-ANPP
    Synonyms
    • 4-ANPP
    • 4-Aminophenyl-1-phenethylpiperidine
    • 4-Anilino-N-phenethylpiperidine
    • Despropionyl fentanyl
    IUPAC N-phenyl-1-(2-phenylethyl)-4-piperidinamine
    Formula C19H24N2
    Molecular weight 280.4 g/mol
    CAS 21409-26-7
    Appearance Powder
    Purity ≥ 98%

    4-ANPP and other chemicals sold on this website are designed and must be used strictly for research and forensic medical examination.

    Adverse properties of have not been studied.

    Storage conditions of this chemical: in a cool and dry place. The stability of this chemical compound can last up to 2 years, under the right storage conditions.

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CAS 21409-26-7: 4-Anilino-N-phenethylpiperidine (ANPP)

 

ANPP is a synthetic chemical compound primarily recognized for its role as an intermediate in the synthesis of various psychoactive substances, particularly …Read more

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Compound Details ; CAS: 21409-26-7 ; Name: 1-Phenethyl-N-phenylpiperidin-4-amine ; Name: 4-ANPP ; Name: 4-ANPP (CRM) ; Name: 4-Aminophenyl-1-phenethylpiperidine.Read more

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CAS 21409-26-7: 4-Anilino-N-phénéthylpipéridine (ANPP)

 

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