Diethyl Ether → HCID 10439569, compound

Participants

Reaction Steps

The polar diastereoisomer of 4-(5-chloro-1H-indol-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide (246 mg, 0.5 mmole) was dissolved in ethyl methyl ketone (10 ml). Chlorotrimethylsilane (95 μl, 0.75 mmole) was added dropwise at RT while stirring. After stirring for 1 hour a small amount of precipitate had formed. Diethyl ether (35 ml) was added to the reaction solution. The reaction solution was then stirred vigorously for 2 hours at RT. An orange precipitate formed. The solid was filtered off under suction, washed with diethyl ether (3×2 ml) and dried in vacuo. The hydrochloride of the polar diastereoisomer of 4-(5-chloro-1H-indol-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide (207 mg, m.p. 183°-185° C., 78%) was thereby obtained as a cinnamon-coloured solid (Example 59).

Provenance & Evidence