Diethyl Ether → 4-(5-Fluoro-1H-indol-3-yl)butanoic acid (4-dimethylamino-4-phenylcyclohexylmethyl)amide hydrochloride

Participants

Reaction Steps

In the manner described for Example 21, 240 mg (0.55 mmol.) of the polar diastereoisomer of 4-(5-fluoro-1H-indol-3-yl)butanoic acid (4-dimethylamino-4-phenylcyclohexylmethyl)amide were also obtained (m.p. 160–163° C.) and were dissolved in 2-butanone (7 ml); chlorotrimethylsilane (105 μl, 0.83 mmol.) was added thereto. There immediately formed a pale precipitate, which was deposited in a tacky manner on the wall of the flask. The solvent was reduced to about 3 ml in vacuo and, after addition of ether (3 ml), vigorous stirring was carried out for 1 h at RT. The solid that formed was filtered off with suction, washed with ether (3×1.5 ml) and dried in vacuo. The hydrochloride of the polar diastereoisomer of 4-(5-fluoro-1H-indol-3-yl)butanoic acid (4-dimethylamino-4-phenylcyclohexylmethyl)amide was thus obtained in the form of a hygroscopic solid in a yield of 234 mg.

Provenance & Evidence