Phenylacetonitrile → 1-n-Butyl-4-cyano-4-phenylpiperidine hydrochloride

HRID 1253361Notes

Reaction equation

HRID 1253361 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:5][CH2:6]Cl.[C:12]1([CH2:18][C:19]#[N:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[OH-].[Na+].[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[ClH:1].[CH2:8]([N:4]1[CH2:5][CH2:6][C:18]([C:19]#[N:20])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:2][CH2:3]1)[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 2

HCID 8794PhenylacetonitrileHCID 39224N,N-Bis(2-chloroethyl)-1-butanamine

Product 1

HCID 704073361-n-Butyl-4-cyano-4-phenylpiperidine hydrochlorideYield 30%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 66133Benzyl triethylammonium chlorideCatalyst

Procedure

Gutkowska, Acta Pol. Pharm. 30, 109-113 (1973), shows the reaction of N,N-bis(2-chloroethyl)-n-butylamine with phenylacetonitrile in the presence of 50% aqueous sodium hydroxide solution and benzyltriethylammonium chloride as catalyst to produce 1-n-butyl-4-cyano-4-phenylpiperidine hydrochloride (30% yield).

Sources & evidence

ORD record
ord-9f0360ac7a134866b21b774dddbc54b8
Source dataset
uspto-grants-1988_05
Patent number
US04748276

Reaction notes

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