Dimethylformamide → HCID 22099417, compound

Participants

Reaction Steps

Under ice-cooling, to 20 ml of a dimethylformamide (DMF) suspension containing 850 mg of 62% sodium hydride was added little by little 5.4 g of N-benzyloxycarbonylamino-2-(4-hydroxyphenyl)ethylamine, and the mixture was stirred at room temperature for 20 minutes. Then, the mixture was ice-cooled, 10 ml of a DMF solution containing 4.5 g of N,N-dibutyl-3-chloropropylamine was added thereto. Further, after stirring the mixture at room temperature for 24 hours, water was added thereto and the mixture was extracted with diethyl ether. The extract was washed and dried, and the solvent was removed from the extract under reduced pressure. The residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=2:1 and then chloroform:ethanol=20:1) to give 5.5 g of N-benzyloxycarbonyl-2-[4-(3-dibutylaminopropyloxy)phenyl]ethylamine (yield: 63%, oily product, IR (film): 3310, 1710 cm-1).

Provenance & Evidence