4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 10078061, compound

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Reaction Steps

A mixture of the diastereoisomers of (4-aminomethyl-1-phenylcyclohexyl)dimethylamine (347 mg, 1.49 mmol.) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (620 mg, 2.2 mmol.) was added to a solution of the potassium salt of 6-(5-fluoro-1H-indol-3-yl)hexanoic acid (430 mg, 1.49 mmol.) in abs. methanol (30 ml), and stirring was carried out for 3 d at RT. For working up, the mixture was concentrated, water (10 ml) and 2M HCl (15 ml) were added to the residue, and washing was carried out with ether (25 ml). The diethyl ether phase was separated off. The aqueous phase and oily drops contained therein were adjusted to pH 11 with 5M NaOH and extracted with EE (4×15 ml). The combined EE 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 (75 g) and purified (eluant: 1500 ml of methanol/EE 1:1). 192 mg of the non-polar diastereoisomer of 6-(5-fluoro-1H-indol-3-yl)hexanoic acid (4-dimethylamino-4-phenylcyclohexylmethyl)amide were obtained (m.p. 52–54° C.).

Provenance & Evidence