Hydrochloric Acid → HCID 13151844, compound

Participants

Reaction Steps

A solution of 4.5 g of sodium nitrite in 10 ml of water is added dropwise at 0°, with stirring, to a suspension of 16 g of N-acetyl-4-(2-amino-4-acetyl-phenyl)-piperidine in 75 ml of concentrated hydrochloric acid and 75 ml of water; stirring is continued at 0° for 2 hours; the reaction solution, which is now clear, is transferred to a dropping funnel precooled to 0°, and is slowly added dropwise to a solution, cooled to 0° and being stirred, of 16 g of copper-I-chloride in 150 ml of semi-concentrated hydrochloric acid. Stirring is maintained at 15° until the evolution of nitrogen has ceased (about 1 hour). An addition of 300 ml of water is made, and extraction is performed three times with 150 ml of ethyl acetate each time. The organic phases are extracted three times at 0° with 150 ml of 2 N sodium hydroxide solution each time; they are then cleared by filtration, washed neutral, dried over sodium sulphate and concentrated in vacuo. The oily N-acetyl-4-(2-chloro-4-acetyl-phenyl)-piperidine obtained in this manner can be used without purification.

Provenance & Evidence