Dimethylformamide → HCID 59222472, compound

Participants

Reaction Conditions

Reaction Steps

The starting material 4-aminomethyl-3-chloro-benzylamine was prepared from 1,4-bis-bromomethyl-2-chloro-benzene as follows. A suspension of 1,4-bis-bromomethyl-2-chloro-benzene (470 mg) and sodiumazide (225 mg) in dimethylformamide (2.5 ml) was stirred at 60° C. for 2 hours. The reaction mixture was then diluted with water and extracted with ether. The combined organic extracts were then washed with water, dried (Na2SO4) and evaporated. Part of the remaining residue (233 mg) was dissolved in methanol (5 ml) and tin(II) chloride (962 mg) was added portionwise at 0° C. The reaction mixture was then stirred at room temperature over night. The solvent was removed and the residue was dissolved in 3N sodium hydroxide (12 ml) and this solution was saturated with sodium chloride and extracted with chloroform. The combined extracts were dried (sodium sulfate) and evaporated and the remaining material was purified by chromatography (dichloromethane/methanol/ammonia 19:1:0.1 and 9:0.9:0.1). 4-Aminomethyl-3-chloro-benzylamine was obtained as light yellow oil (76 mg).

Provenance & Evidence