N-tert-butylpiperidine-4-carboxamide → 1-(5-Amino-2-methyl-benzyl)-piperidine-4-carboxylic acid tert-butylamide

HRID 1486704Notes

Reaction equation

HRID 1486704 reaction equation
CC1C=CC([N+]([O-])=O)=CC=1C=O.C(NC(C1CCNCC1)=O)(C)(C)C.[C:26]([NH:30][C:31]([CH:33]1[CH2:38][CH2:37][N:36]([CH2:39][C:40]2[CH:45]=[C:44]([N+:46]([O-])=O)[CH:43]=[CH:42][C:41]=2[CH3:49])[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]>>[C:26]([NH:30][C:31]([CH:33]1[CH2:38][CH2:37][N:36]([CH2:39][C:40]2[CH:45]=[C:44]([NH2:46])[CH:43]=[CH:42][C:41]=2[CH3:49])[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]

Participants

4

Reactant 3

HCID 7175833N-tert-butylpiperidine-4-carboxamideHCID 126541452-Methyl-5-nitrobenzaldehydeHCID 867065361-(2-Methyl-5-nitro-benzyl)-piperidine-4-carboxylic acid tert-butylamide

Product 1

HCID 867065351-(5-Amino-2-methyl-benzyl)-piperidine-4-carboxylic acid tert-butylamide

Procedure

The title compound is prepared according to the reactions described for BB-5 above starting from 2-methyl-5-nitro-benzaldehyde and piperidine-4-carboxylic acid tert-butylamide yielding after reductive amination 1-(2-methyl-5-nitro-benzyl)-piperidine-4-carboxylic acid tert-butylamide; LC-MS A: tR=0.62 min; [M+H]+=334.21 followed by reduction with stannous chloride the title compound; LC-MS A: tR=0.44 min; [M+H]+=304.28.

Workup

  1. customThe title compound is prepared

Sources & evidence

ORD record
ord-43010248afc84310995d8406544eb9d5
Source dataset
uspto-grants-2016_08
Patent number
US09428456B2

Reaction notes

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