N-tert-butylpiperidine-4-carboxamide → 1-(3-Amino-5-bromo-benzyl)-piperidine-4-carboxylic acid tert-butylamide

HRID 1486700Notes

Reaction equation

HRID 1486700 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:10]([O-])=O)[CH:9]=1)[CH:5]=O.[C:13]([NH:17][C:18]([CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>>[C:13]([NH:17][C:18]([CH:20]1[CH2:25][CH2:24][N:23]([CH2:5][C:4]2[CH:3]=[C:2]([Br:1])[CH:9]=[C:8]([NH2:10])[CH:7]=2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

3

Reactant 2

HCID 7175833N-tert-butylpiperidine-4-carboxamideHCID 167439663-Bromo-5-nitrobenzaldehyde

Product 1

HCID 867065321-(3-Amino-5-bromo-benzyl)-piperidine-4-carboxylic acid tert-butylamide

Procedure

The title compound is prepared according to the reactions described above starting from 3-bromo-5-nitro-benzaldehyde and piperidine-4-carboxylic acid tert-butylamide yielding after reductive amination BB-10a; LC-MS A: tR=0.65 min; [M+H]+=398.00 followed by reduction with stannous chloride the title compound; LC-MS A: tR=0.60 min; [M+H]+=369.67.

Workup

  1. customThe title compound is prepared

Sources & evidence

ORD record
ord-44ecdcb15d0e4960801a9bb406124468
Source dataset
uspto-grants-2016_08
Patent number
US09428456B2

Reaction notes

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