Hydrochloric Acid → HCID 15631331, compound

Participants

Reaction Steps

A mixture of 2.00 g (13.4 mmol) of 1,2,3,4-tetrahydro-8-quinolinol (see Example 7A), 1.69 g (20.0 mmol, 1.5 eq.) of finely powdered sodium bicarbonate and 1.75 ml (14.7 mmol, 1.1 eq.) of benzyl bromide in 40 ml of hexamethylphosphoramide was stirred for 24 hours at room temperature under argon. The following work-up was carried out under conditions of minimum air exposure. Solvents and solutions were bubbled with nitrogen prior to use. The reaction mixture was diluted with 300 ml of 1:1 ether:petroleum ether and washed with five 100 ml portions of water and 100 ml of brine, dried over sodium sulfate and evaporated to obtain a tan solid. The solid was immediately dissolved in 10 ml of methanol, treated with 10 ml of hydrogen chloride-saturated methanol and diluted with 200 ml of ether. The precipitate was filtered, washed with ether, and dried under vacuum for 20 hours to afford 3.19 g of the title compound as an ivory solid; melting point 192°-194° C. (decomposition from 175° C.). 1H NMR indicated that this material contained 0.16 equivalents of methanol.

Provenance & Evidence