4-Fluorobenzenesulfonyl chloride → N1-[4-(aminomethyl)cyclohexyl]methyl-4-fluoro-1-benzenesulfonamide

HRID 1250837Notes

Reaction equation

HRID 1250837 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.[NH2:12][CH2:13][CH:14]1[CH2:19][CH2:18][CH:17]([CH2:20][NH2:21])[CH2:16][CH2:15]1.C(N(C(C)C)CC)(C)C>ClCCl>[NH2:12][CH2:13][CH:14]1[CH2:19][CH2:18][CH:17]([CH2:20][NH:21][S:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 173541,4-CyclohexanedimethanamineHCID 81531Diisopropylethylamine

Product 1

HCID 18440301N1-[4-(aminomethyl)cyclohexyl]methyl-4-fluoro-1-benzenesulfonamideYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.37 g of 4-fluorophenylsulfonyl chloride (12.2 mmol) in 30 ml of dichloromethane was added over 10 minutes to a stirred solution of 5.20 g of 1,4-bis-aminomethylcyclohexane (36.6 mmol) and 3.15 g of diisopropylethylamine (24.4 mmol) in 100 ml of dichloromethane at room temperature. The reaction mixture was stirred at room temperature for 16 hours, concentrated, and chromatographed on 200 g of silica packed with 5% MeOH (containing 2M NH3)-CHCl3, eluted with 5%, 7.5%, 10% (1 liter each) to give 3.63 g of the desired product.

Workup

  1. concentrationconcentrated
  2. customchromatographed on 200 g of silica
  3. washeluted with 5%, 7.5%, 10% (1 liter each)

Sources & evidence

ORD record
ord-f9e0321df33244aaa8c5d047eb696df2
Source dataset
uspto-grants-2002_01
Patent number
US06340683B1

Reaction notes

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