4-Cyanobenzenesulfonyl chloride → 7-(n-Butyl)-3-[(4-cyanophenyl)sulfonyl]-9,9-dimethyl-3,7-diazabicyclo[3.3.1]nonane hydrochloride

HRID 1900626Notes

Reaction equation

HRID 1900626 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([Cl:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[CH2:13]([N:17]1[CH2:24][CH:23]2[C:25]([CH3:27])([CH3:26])[CH:19]([CH2:20][NH:21][CH2:22]2)[CH2:18]1)[CH2:14][CH2:15][CH3:16]>ClCCl>[ClH:12].[CH2:13]([N:17]1[CH2:18][CH:19]2[C:25]([CH3:26])([CH3:27])[CH:23]([CH2:22][N:21]([S:9]([C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)(=[O:11])=[O:10])[CH2:20]2)[CH2:24]1)[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 394974-Cyanobenzenesulfonyl chlorideHCID 143690087-(n-Butyl)-9,9-dimethyl-3,7-diazabicyclo[3,3,1]nonane

Product 1

HCID 98445327-(n-Butyl)-3-[(4-cyanophenyl)sulfonyl]-9,9-dimethyl-3,7-diazabicyclo[3.3.1]nonane hydrochlorideYield 53.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.5 g of 4-cyanobenzenesulfonyl chloride in 20 ml of dichloromethane was added dropwise with ice-cooling to a solution of 2.37 g of 7-(n-butyl)-9,9-dimethyl-3,7-diazabicyclo[3.3.1]nonane in 30 ml of dichloromethane. The ice-cooling was then removed, and the reaction mixture was stirred at room temperature for one hour. The hydrochloride of the title compound was thereupon deposited as a white precipitate. The crystals were filtered out with suction and dried at 60° C. in a vacuum drying oven. 2.5 g of 7-(n-butyl)-3-[(4-cyanophenyl)sulfonyl]-9,9-dimethyl-3,7-diazabicyclo[3.3.1]nonane hydrochloride having a melting point of 98° to 99° C. were obtained.

Workup

  1. customwas then removed
  2. filtrationThe crystals were filtered out with suction
  3. customdried at 60° C. in a vacuum
  4. customdrying oven

Sources & evidence

ORD record
ord-1f962c56fc104e4db9332b210018a58b
Source dataset
uspto-grants-1996_11
Patent number
US05576327

Reaction notes

Loading…