Indole-3-Acetic Acid → HCID 10002558, compound

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Reaction Steps

The non-polar diastereoisomer of (4-aminomethyl-1-phenylcyclohexyl)dimethylamine (239 mg, 1.03 mmol.) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (428 mg, 1.6 mmol.) were added to a solution of 2-(1H-indol-3-yl)acetic acid (180 mg, 1.03 mmol.) in abs. methanol, and stirring was carried out for 24 h at RT. For working up, the mixture was concentrated and the residue was suspended in water (20 ml); 2M HCl (1.5 ml, pH 3) was added, with stirring, and washing was carried out with ether (3×5 ml). The aqueous phase was adjusted to pH 11 with 5M NaOH and extracted with EE (4×10 ml). The organic phase was washed with 1M NaOH (3 ml), dried, filtered and concentrated. The residue was the non-polar diastereoisomer of N-(4-dimethylamino-4-phenylcyclohexylmethyl)-2-(1H-indol-3-yl)acetamide, which was obtained in the form of a solid in a yield of 395 mg (98%). These 395 mg (1.01 mmol.) were dissolved in 2-butanone (5 ml) and acetone (3 ml), and chlorotrimethylsilane (193 μl, 1.52 mmol.) was added thereto. There immediately formed a colourless precipitate, which turned slightly beige in colour at RT. The precipitate was filtered off, washed with cold 2-butanone (2×1 ml) and cold ether (2×2 ml) and dried in vacuo. The hydrochloride of N-(4-dimethylamino-4-phenylcyclohexylmethyl)-2-(1H-indol-3-yl)acetamide was obtained in a yield of 341 mg (light-beige solid, m.p. 128–135° C.).

Provenance & Evidence