Ammonia → 1-[4-(Ethylsulfonyl)phenyl]methanamine

HRID 750307Notes

Reaction equation

HRID 750307 reaction equation
[CH2:1]([S:3]([C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)(=[O:5])=[O:4])[CH3:2].N>CO.O1CCCC1.[Ni]>[CH2:1]([S:3]([C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH2:11])=[CH:8][CH:7]=1)(=[O:5])=[O:4])[CH3:2]

Participants

6

Reactant 2

HCID 222AmmoniaHCID 230606754-(Ethanesulfonyl)benzonitrile

Product 1

HCID 179666261-[4-(Ethylsulfonyl)phenyl]methanamineYield 82%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

[Step 3] To a mixture of 4-ethanesulfonylbenzonitrile (500 mg) in methanol (6 ml) and tetrahydrofuran (2 ml) was added 28% aqueous ammonia (1 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 4-ethanesulfonylbenzylamine (408 mg, 82%).

Workup

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

Sources & evidence

ORD record
ord-b4dc2d6121d44a029e990354d279ed5b
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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