Phosphorus oxide (P4O10) → HCID 21286397, compound

Participants

Reaction Steps

Solid N-chloroacetyl-1-phenyl-2-(3-methoxyphenyl)ethylamine (72.0 g, 0.23 mol) was added with stirring to a suspension of phosphorus pentoxide (261.1 g, 1.84 mol) in xylene (6 L) maintained under nitrogen at reflux, and the resulting mixture was refluxed for 1 hr, after which it was allowed to cool to ambient temperature. The xylene was decanted off and the residue was cooled to 0° C. Ice cold water (4 L) was added to the residue, and the resulting solution was then basified to pH 11 with 50% NaOH, and then extracted, first with ether (1 L) and then with chloroform (2×750 ml). The combined organic extracts were dried over MgSO4, evaporated to a dark oil which was dissolved in a mixture of acetone (200 ml) and ether (100 ml) and then acidified with HCl gas. Upon standing, the treated extracts yielded yellowish solid crystals, which were collected by filtration to give 48.8 g (64%) of 1-chloromethyl-3,4-dihydro-6-methoxy-3-phenylisoquinoline hydrochloride. An analyticl sample recrystallized from acetone had a mp. 174°-175° C.

Provenance & Evidence