Benzylamine → N-benzylpiperidin-4-amine

Reaction equation

[C:1]([BH3-])#[N:2].[Na+].[CH2:5]([NH2:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[CH2:5]([NH:12][CH:6]1[CH2:5][CH2:1][NH:2][CH2:8][CH2:7]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

Reactant 2

HCID 7504Benzylamine

HCID 5003444Sodium cyanoborohydride

Product 1

HCID 3016528N-benzylpiperidin-4-amine

Procedure

The compounds of formula A and G are prepared as is described in Reaction Sequences 1 and 2. Compound G is then treated with sodium cyanoborohydride, optionally in the presence of benzylamine, to produce the 4-(benzyl)amino piperidine which is subsequently coupled with the compound of formula A to produce the benzyl derivative (formula G"). The compound of formula G" is then hydrogenated using, for instance, palladium-on-carbon catalyst to produce the compound of formula I.

Workup

customThe compounds of formula A and G are prepared
customas is described in Reaction Sequences 1 and 2

Sources & evidence

ORD record: ord-746d12cd9afa47d7b19365652c6d5842
Source dataset: uspto-grants-1985_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04499100

Reaction notes

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