Methylamine → HCID 15491311, compound

Participants

Reaction Steps

In a round-bottomed flask fitted with a reflux condenser and a thermometer are introduced 1.5 g (3 mmoles) of {4-[2-(3,5-Bis-trifluoromethyl-benzyloxy)-1-phenyl-ethyl]-piperazin-1-yl}-acetic acid (compound 229 prepared at example 1.4.2 above), 7 ml of THF and 7 ml of acetonitrile. Then 1.85 ml (3.7 mmoles) of a 2M solution of methylamine in THF are added, followed by 234 mg (1.5 mmoles) of HOBT, 1.33 ml (7.6 mmoles) of diisopropylethylamine and 880 mg (4.3 mmoles) of DCC. The mixture is stirred until completion of the reaction, and filtered. Volatile substances are removed under reduced pressure, and the residue is partitioned between ethyl acetate and 0.1 N sodium hydroxide. The organic phase is washed with brine, dried over magnesium sulfate and volatile substances are removed under reduced pressure. This yields crude 2-{4-[2-(3,5-Bis-trifluoromethyl-benzyloxy)-1-phenyl-ethyl]-piperazin-1-yl}-N-methyl-acetamide (compound 292) which is directly converted into its dimaleate salt in 2-butanone (1.44 g of a white solid; yield 65%).

Provenance & Evidence