4-Fluorobenzenesulfonyl chloride → HCID 19044692, compound

HRID 1682448Notes

Reaction equation

HRID 1682448 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:12]([N:16]1[CH2:23][CH:22]2[C:24]([CH3:26])([CH3:25])[CH:18]([CH2:19][NH:20][CH2:21]2)[CH2:17]1)[CH2:13][CH2:14][CH3:15]>ClCCl>[CH2:12]([N:16]1[CH2:17][CH:18]2[C:24]([CH3:25])([CH3:26])[CH:22]([CH2:21][N:20]([S:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)(=[O:10])=[O:9])[CH2:19]2)[CH2:23]1)[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 143690087-(n-Butyl)-9,9-dimethyl-3,7-diazabicyclo[3,3,1]nonane

Product 1

HCID 19044692HCID 19044692, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 7.2 g of 4-fluorobenzenesulfonyl chloride in 10 ml of dichloromethane was added dropwise with ice-cooling to a solution of 7.8 g of 7-(n-butyl)-9,9-dimethyl-3,7-diazabicyclo[3.3.1]nonane in 40 ml of dichloromethane. The ice-cooling was then removed, and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was worked up by adding aqueous sodium bicarbonate solution and extracting twice with dichloromethane. The combined dichloromethane extracts were dried with magnesium sulfate and concentrated. 12.9 g of 7-(n-butyl)-3-[(4-fluorophenyl)sulfonyl]-9,9-dimethyl-3,7-diazabicyclo[3.3.1]nonane were obtained.

Workup

  1. customwas then removed
  2. additionby adding aqueous sodium bicarbonate solution
  3. extractionextracting twice with dichloromethane
  4. dry with materialThe combined dichloromethane extracts were dried with magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d866c69edb8f4bb185faee913a874967
Source dataset
uspto-grants-1997_06
Patent number
US05635511

Reaction notes

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