1-Chloro-4-nitrobenzene → HCID 12874832, compound

Participants

Reaction Conditions

Reaction Steps

26 ml of dimethylsulfoxide were added to 2.6 g of a 50% dispersion of sodium hydride in oil and the mixture was stirred at 60°-65° C. for 30 minutes and was then cooled to 22° C. 5.8 g of N,N-dimethyl-3-phenyl-3-hydroxy-propanamine hydrochloride were added to the mixture which was then stirred for 10 minutes at 25° C. Then, 8.95 g of p-chloronitrobenzene were added to the mixture which was stirred at room temperature for 15 minutes. The mixture was extracted with methylene chloride and the organic phase was washed with water, dried, filtered and evaporated to dryness under reduced pressure to obtain 17 g of raw product. The latter was extracted 3 times with 200 ml of N hydrochloric acid and the neutral fraction was eliminated 3 times with 200 ml of ether. The combined aqueous phases were made alkaline with excess concentrated ammonium hydroxide and the precipitate was extracted with methylene chloride. The extract was dried, filtered and evaporated to dryness under reduced pressure to obtain 7.7 g of N,N-dimethyl-γ-(4-nitrophenoxy)benzene-propanamine.

Provenance & Evidence