Acetic Acid → (R)-N-[2-(4-Methoxybenzoylamino)-2-phenylethyl]-1-isopropylpiperidine-4-carboxamide

Participants

Reaction Steps

(Alkylation Method A) (R)-N-[2-(4-Methoxybenzoylamino)-2-phenylethyl]piperidine-4-carboxamide trifluoroacetate (0.50 g, 1.0 mmol), acetone (4.5 mL, 61 mmol), acetic acid (0.28 mL, 4.9 mmol), and sodium cyanoborohydride (0.32 g, 5.1 mmol) were combined in methanol, and stirred. After 4 h, TLC (79% CH2Cl2, 19% methanol, 1% NH4OH) indicated reaction completion. The solution was diluted with methanol (100 mL), and passed through H+ form ion exchange resin (Varian SCX cartridge, Catalog #1225-6035) washed with methanol, and then with 2 M NH3 in methanol to collect the product. The product was recrystallized from methanol and ether to afford 0.30 g (70%) of a white crystalline solid

Provenance & Evidence