Benzenesulfonic Acid → HCID 22141137, compound

HRID 428894Notes

Reaction equation

HRID 428894 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([S:34]([OH:37])(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CC(=O)CC>[C:28]1([S:34]([OH:37])(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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 7371Benzenesulfonic AcidHCID 9864893HCID 9864893, compound

Product 1

HCID 22141137HCID 22141137, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

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, 53.88 g, 0.14 mol) in 2-butanone (480 ml) was heated under reflux. To the solution was added a solution of benzenesulfonic acid (22.17 g, 0.14 mol) in 2-butanone (50 ml) and the reaction mixture was heated under reflux for 30 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 beige crystalline solid (73.55 g, 97%).

Workup

  1. temperatureunder reflux
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for 30 min
  4. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-f4fff7e891ba4028b908223419997fd3
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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