Ammonia methanol → 1-Piperidinecarboxylic acid, 4-(aminomethyl)-4-[(phenylmethoxy)methyl]-, 1,1-dimethylethyl ester

HRID 1748308Notes

Reaction equation

HRID 1748308 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1([C:23]#[N:24])[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.N>[Ni].CO>[NH2:24][CH2:23][C:10]1([CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 21705897Ammonia methanolHCID 53485182tert-Butyl 4-[(benzyloxy)methyl]-4-cyanopiperidine-1-carboxylate

Product 1

HCID 672364511-Piperidinecarboxylic acid, 4-(aminomethyl)-4-[(phenylmethoxy)methyl]-, 1,1-dimethylethyl esterYield 79%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a slurry of Raney nickel (1 g, 10% w/w) in methanol are added tert-butyl 4-[(benzyloxy)methyl]-4-cyanopiperidine-1-carboxylate (10 g, 30.3 mmol) and methanol/NH3 (1 mL). The reaction mixture is stirred at room temperature under 60 psi of H2 for 16 h. Then the reaction mixture is filtered through a pad of Celite and the filtrate is concentrated to afford the title compound (8 g, 79%) as a colorless liquid.

Workup

  1. filtrationThen the reaction mixture is filtered through a pad of Celite
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-85d246bceeda43b5ba7db3ab09b45401
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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