N-Benzylnormechlorethamine → 4-Piperidinecarbonitrile, 4-phenyl-1-(phenylmethyl)-, hydrochloride (1:1)

HRID 1253362Notes

Reaction equation

HRID 1253362 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:5][CH2:6]Cl.[C:15]1([CH2:21][C:22]#[N:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[ClH:1].[CH2:8]([N:4]1[CH2:5][CH2:6][C:21]([C:22]#[N:23])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:2][CH2:3]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 5928N-BenzylnormechlorethamineHCID 8794Phenylacetonitrile

Product 1

HCID 126520624-Piperidinecarbonitrile, 4-phenyl-1-(phenylmethyl)-, hydrochloride (1:1)

Procedure

Rylski, F. Gajewski and Z. Kamonski, Acta Pol. Pharm. 31, 577-582 (1974), show two methods for the conversion of N,N-bis(2-chloroethyl)benzylamine by reaction with phenylacetonitrile to produce 1-benzyl-4-cyano4-phenylpiperidine hydrochloride, the first method in a sodium hydroxide-toluene system resulting in a 63% yield of product melting at 253°-254° C. and the second method in a catalytic process using benzyltriethylammonium chloride in 50% aqueous sodium hydroxide resulting in a 61% yield of product melting at 254°-255° C. (Eisleb, supra, 259°-260° C.).

Sources & evidence

ORD record
ord-d359fb6ecf8e43c58675a679f5341a97
Source dataset
uspto-grants-1988_05
Patent number
US04748276

Reaction notes

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