Benzenesulfonyl chloride, 3,4-dichloro- → 7-(n-Butyl)-3-[(3,4-dichlorophenyl)sulfonyl]-9,9-dimethyl-3,7-diazabicyclo[3,3,1]nonane hydrochloride

HRID 703475Notes

Reaction equation

HRID 703475 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[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:1].[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:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)(=[O:11])=[O:10])[CH2:20]2)[CH2:24]1)[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 143690087-(n-Butyl)-9,9-dimethyl-3,7-diazabicyclo[3,3,1]nonane

Product 1

HCID 221503507-(n-Butyl)-3-[(3,4-dichlorophenyl)sulfonyl]-9,9-dimethyl-3,7-diazabicyclo[3,3,1]nonane hydrochlorideYield 127%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.8 g (=0.0114 mol) 3,4-dichlorobenzene sulfonic acid chloride in 20 ml dichloromethane was added dropwise with ice cooling to a solution of 2.4 g (=0.0114 mol) 7-(n-butyl)-9,9-dimethyl-3,7-diazabicyclo[3,3,1]nonane (=substance No. C1 in the following Table C) in 40 ml dichloromethane. Then the ice bath was removed and the reaction mixture stirred further for 3 hours at room temperature. The hydrochloride of the title compound thereby precipitated as a white precipitate. In order to complete crystallization, the reaction mixture was allowed to stand 12 more hours in a refrigerator. Then the crystals were separated by suction filtration and dried at 60° C. in a vacuum drier. 3.3 g 7-(n-butyl)-3-[(3,4-dichlorophenyl)sulfonyl]-9,9-dimethyl-3,7-diazabicyclo[3,3,1]nonane hydrochloride with a melting point of 170°-173° C. were obtained.

Workup

  1. customThen the ice bath was removed
  2. customThe hydrochloride of the title compound thereby precipitated as a white precipitate
  3. customcrystallization
  4. customThen the crystals were separated by suction filtration
  5. customdried at 60° C. in a vacuum drier

Sources & evidence

ORD record
ord-872096aadfe244e4af44eefe02f735a5
Source dataset
uspto-grants-1991_01
Patent number
US04983611

Reaction notes

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