Triethylamine → 6-benzensulfonylamino-1-benzyl-4-methylhexahydro-1H-1,4-diazepine

HRID 374115Notes

Reaction equation

HRID 374115 reaction equation
[C:1]1([S:7]([N:10]2[CH2:12][CH:11]2[CH2:13]Br)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15]([NH:22][CH2:23][CH2:24][NH:25][CH3:26])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:1]1([S:7]([NH:10][CH:11]2[CH2:13][N:22]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:23][CH2:24][N:25]([CH3:26])[CH2:12]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 243646Aziridine, 2-(bromomethyl)-1-(phenylsulfonyl)-HCID 10920861N~1~-Benzyl-N~2~-methylethane-1,2-diamine

Product 1

HCID 100670376-benzensulfonylamino-1-benzyl-4-methylhexahydro-1H-1,4-diazepineYield 22.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1-benzenesulfonyl-2-bromomethylethylenimine (27.2 g), N-benzyl-N'-methylethylenediamine (16.2 g), triethylamine (19.9 g) and chloroform (350 ml) is refluxed with stirring for 5 hours. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel chromatography to give the title compound (7.9 g) as an oil.

Workup

  1. temperatureis refluxed
  2. customThe solvent is evaporated under reduced pressure
  3. customthe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-57966f3d65c846eb9165fb83d19ec86a
Source dataset
uspto-grants-1992_11
Patent number
US05166341

Reaction notes

Loading…