Chlorotrimethylsilane → HCID 10369286, compound

Participants

Reaction Steps

A mixture of the diastereoisomers of (4-aminomethyl-1-phenylcyclohexyl)dimethylamine (152 mg, 0.65 mmol.) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (207.5 mg, 0.75 mmol.) was added to a solution of 6-(5-chloro-1H-indol-3-yl)hexanoic acid (174 mg, 0.65 mmol.) in abs. methanol (5 ml), and stirring was carried out for 2 d at RT. For working up, the mixture was concentrated, water (15 ml) was added to the residue, the pH was adjusted to 11 with 5M NaOH and extraction was carried out with EE (4×15 ml). The combined extracts were washed with 1M NaOH (2×2 ml), dried, filtered and concentrated. The residue was a diastereoisomeric mixture of the bases of the target product, which was separated by flash chromatography on silica gel (35 g) and purified (eluant: 600 ml of methanol/EE 1:1). The resulting non-polar diastereoisomer (110 mg, 0.23 mmol.) was dissolved in 2-butanone (5 ml), and chlorotrimethylsilane (44 μl, 0.35 mmol.) was added thereto. There immediately formed a white precipitate, which after 15 min. was deposited in a tacky manner on the wall of the flask. The solvent was reduced to about 0.5 ml in vacuo, ether (2 ml) was added to the residue, and vigorous stirring was carried out for 1 h. The solid that formed was filtered off with suction, washed with ether (2×1 ml) and dried in vacuo. The hydrochloride of the non-polar diastereoisomer of 6-(5-chloro-1H-indol-3-yl)hexanoic acid (4-dimethylamino-4-phenylcyclohexylmethyl)amide was thus obtained in the form of a slightly hygroscopic solid in a yield of 124 mg (m.p. 135–145° C.).

Provenance & Evidence