Hydrochloric Acid → HCID 68828835, compound

Participants

Reaction Steps

As described for Example 8, less polar diastereoisomers of {4-[3-(1H-indol-3-yl)-propenyl]-1-phenylcyclohexyl}dimethylamine were not obtained cleanly. For purification, 750 mg non-polar crude product were suspended in 95 ml water and 1 ml 85% by weight phosphoric acid. The suspension was shaken with diethyl ether (3×20 ml), the diethyl ether was decanted off in each case and the solid subsequently suction filtered and washed with diethyl ether (10×3 ml). The solid was dried, dissolved in DMF and 1M NaOH (10 ml) added. The alkaline solution was extracted with EE (5×10 ml). The combined EE phases were dried, filtered and evaporated. The residue obtained, 309 mg of a less polar diastereoisomer of {4-[3-(1H-indol-3-yl)-propenyl]-1-phenylcyclohexyl}dimethylamine (viscous oil), was dissolved in 2-butanone (5 ml), and subsequently chlorotrimethylsilane (0.33 ml, 2.6 mmole) was added and the mixture stirred overnight at RT. After adding diethyl ether (3 ml) and a further 30 min, the precipitated hydrochloride of a less polar diastereoisomer of 4-[3-(1H-indol-3-yl)-propenyl]-1-phenylcyclohexyl}dimethylamine was suction filtered and isolated in a yield of 137 mg (beige solid, mp. 138 to 142° C.).

Provenance & Evidence