1,4-Cyclohexanedimethanamine → N'-[4-(aminomethyl)cyclohexyl]methyl-N,N-dimethylsulfamide

HRID 457675

Reaction equation

HRID 457675 reaction equation
[CH3:1][N:2]([CH3:7])[S:3](Cl)(=[O:5])=[O:4].[NH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][NH2:17])[CH2:12][CH2:11]1.C(N(C(C)C)CC)(C)C>ClCCl>[NH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][NH:17][S:3]([N:2]([CH3:7])[CH3:1])(=[O:5])=[O:4])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 173541,4-CyclohexanedimethanamineHCID 81531DiisopropylethylamineHCID 83372Dimethylsulphamoyl chloride

Product 1

HCID 22254077N'-[4-(aminomethyl)cyclohexyl]methyl-N,N-dimethylsulfamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethylsulfamoyl chloride (one mol-equivalent, ClSO2N(CH3)2) was added to a stirred solution of 1,4-bis-aminomethylcyclohexane (3 mol-equivalents) and diisopropylethylamine (1 mol-equivalent) in dichloromethane at 0° C. The reaction mixture was stirred at room temperature for 24 hours, concentrated under reduced pressure and chromatographed (silica) to give the desired product as viscous oils. (Scheme 1A).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customchromatographed (silica)

Sources & evidence

ORD record
ord-5e70ce1d4c6c492c8f28d8f2334634c4
Source dataset
uspto-grants-2007_03
Patent number
US07189720B2

Linked notes

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