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

HRID 413663Notes

Reaction equation

HRID 413663 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-1c4980a30bde4d3e8e831941d46524ea
Source dataset
uspto-grants-2003_05
Patent number
US06569856B2

Reaction notes

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