p-Toluenesulfonic acid → HCID 22141161, compound

HRID 428895Notes

Reaction equation

HRID 428895 reaction equation
[CH3:1][C:2]1([C:17]2[CH:18]=[C:19]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:6]2.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34]([OH:37])(=[O:36])=[O:35])=[CH:30][CH:29]=1>C(OCC)(=O)C>[C:28]1([CH3:38])[CH:29]=[CH:30][C:31]([S:34]([OH:37])(=[O:35])=[O:36])=[CH:32][CH:33]=1.[CH3:1][C:2]1([C:17]2[CH:18]=[C:19]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:6]2

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 9864893HCID 9864893, compound

Product 1

HCID 22141161HCID 22141161, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
10 °C

Procedure

A solution of N-(3-{6-methyl-3-(3-phenylpropyl)-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide (Example 1, 25.00 g, 65 mmol) in ethyl acetate (250 ml) was heated under reflux. To the solution was added para-toluenesulfonic acid (12.36 g, 72 mmol) and the reaction mixture was heated under reflux for 60 min before cooling to 10° C. over a 2 h period. The resulting precipitate was collected by filtration to afford the title compound as a white solid (35.46 g, 95%).

Workup

  1. temperatureunder reflux
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for 60 min
  4. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-02b2b1dd9a484626b07c2f1c13d908db
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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