Pyridine → 2-Amino-N-cyclohexyl-N-methylbenzenesulfonamide

HRID 852231Notes

Reaction equation

HRID 852231 reaction equation
[CH:1]1(CN)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18](Cl)(=[O:20])=[O:19])([O-])=O.[N:22]1C=CC=C[CH:23]=1>C(OCC)(=O)C>[NH2:9][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18]([N:22]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[CH3:23])(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 76688Cyclohexanemethylamine

Product 1

HCID 1168142-Amino-N-cyclohexyl-N-methylbenzenesulfonamideYield 60%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of cyclohexylmethylamine (0.57 g, 5 mmol) in pyridine (8 ml) was added slowly at 0° C. 2-nitrobenzenesulfonyl chloride (1.10 g, 5 mmol) and the reaction mixture was allowed to warm to room temperature and stirred overnight. The pyridine was removed under reduced pressure and the crude mixture obtained was diluted with ethyl acetate and washed with hydrochloric acid solution (25 ml), water (25 ml), brine (25 ml) and dried over sodium sulphate. The solvent was removed under reduced pressure and the resulting crude oil (1.40 g) was dissolved in ethanol and hydrogenated in the presence of a catalytic amount of Raney-Ni®. The catalyst was removed by filtration through Celite® and the solvent was eliminated under reduced pressure to yield a yellow solid (0.80 g, 60%).

Workup

  1. customThe pyridine was removed under reduced pressure
  2. customthe crude mixture obtained
  3. washwashed with hydrochloric acid solution (25 ml), water (25 ml), brine (25 ml)
  4. dry with materialdried over sodium sulphate
  5. customThe solvent was removed under reduced pressure
  6. dissolutionthe resulting crude oil (1.40 g) was dissolved in ethanol and hydrogenated in the presence of a catalytic amount of Raney-Ni®
  7. customThe catalyst was removed by filtration through Celite®

Sources & evidence

ORD record
ord-d7397effb1144fe6ba7d6c9b91068a6f
Source dataset
uspto-grants-2007_08
Patent number
US07253171B2

Reaction notes

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