Ammonia → 1-(4-Aminomethylbenzenesulfonyl)piperidine-4-carboxylic acid ethyl ester

HRID 750312Notes

Reaction equation

HRID 750312 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2].N>C(O)C.O1CCCC1.[Ni]>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][NH2:22])=[CH:17][CH:16]=2)(=[O:13])=[O:14])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 222AmmoniaHCID 38542421-(4-Cyanobenzenesulfonyl)piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 691577331-(4-Aminomethylbenzenesulfonyl)piperidine-4-carboxylic acid ethyl esterYield 77%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

[Step 2] To a mixture of 1-(4-cyanobenzenesulfonyl)piperidine-4-carboxylic acid ethyl ester (1.36 g) in ethanol (84 ml) and tetrahydrofuran (14 ml) was added 28% aqueous ammonia (3 ml) and then Raney nickel (500 mg) was added. Under a hydrogen pressure (0.5 Mpa), the mixture was stirred at room temperature for 2 hrs., and undesired substances were removed by filtration. The filtrate was concentrated under reduced pressure to give 1-(4-aminomethylbenzenesulfonyl)piperidine-4-carboxylic acid ethyl ester (1.05 g, 77%).

Workup

  1. custom, and undesired substances were removed by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e56ebbc421664cd19e0d9cbb2970ebae
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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