Hydrochloric Acid → HCID 21469814, compound

Participants

Reaction Steps

Combine N-acetyl-4-aminobenzophenone (250 g, 1.05 mol), 2-diethylaminoethyl chloride hydrochloride (207.5 g, 1.20 mol), and 85% potassium hydroxide (140 g, 2.12 mol) in acetone (3 L). Heat to reflux. After 2 hours, cool and filter. Evaporate the filtrate in vacuo to give a residue. Combine the residue and t-butyl methyl ether (1 L) and water (2 L). Add aqueous 1M hydrochloric acid solution until the pH is about 2.5. Separate the aqueous layer and extract several times with t-butyl methyl ether. Adjust the pH of the aqueous layer to 10 using aqueous 50% sodium hydroxide solution. Extract the aqueous layer twice with dichloromethane. Dry the combined dichlormethane layers over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with ethyl acetate, 5/95 methanol/ethyl acetate, 10/90 methanol/ethyl acetate to give the title compound: Rf =0.36 (silica gel, 2/8/0.1 methanol/ethyl acetate/triethylamine).

Provenance & Evidence