Ethanol → HCID 4086642, compound

Participants

Reaction Conditions

Reaction Steps

1-(4-Acetamidothiobenzoyl)piperidine (131.2 g, 0.5 mole), ethanol (500 ml), water (1 l) and concentrated sulphuric acid (125 ml) were mixed together and refluxed for 16 hours with stirring; nearly all the solid dissolved during the first hour. The reaction mixture was cooled to about 40°C and filtered quickly to remove any insoluble material. The filtrate was then made alkaline with 6N sodium hydroxide solution using external ice-cooling. The yellow crystalline solid was filtered off, washed with water and dried in vacuo at a temperature of under 50°C. Recrystallisation of the crude product (91 g; m.p. 162°-164°) by dissolving in 6 volumes of warm chloroform (about 546 ml) followed by adding 5 volumes of petroleum ether (b.p. 40°-60°) (about 455 ml) yielded yellow crystals (85 g; 77.3%), m.p. 164°-165°.

Provenance & Evidence