Ethyl chloroformate → N-[(S)-2-(3,4-Dichlorophenyl)-4-[4-[(S)-2-methylsulfinylphenyl]-1-piperidinyl]butyl]-N-ethyl-3-cyano-1-naphthamide

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Reaction Steps

Using standard acylation conditions, 3-cyano-1-naphthoic acid (0.118 g) was converted to the acid chloride and reacted with N-[(S)-2-(3,4-dichlorophenyl)-4-[4-[(S)-2-methylsulfinylphenyl]-1-piperidinyl]butyl]-N-ethylamine (0.336 g) (prepared according to methods described for N-[(S)-2-(3,4-dichlorophenyl)-4-[4-[(S)-2-methylsulfinylphenyl]-1-piperidinyl]butyl]-N-methylamine, except ethyl chloroformate was used in place of acetyl chloride for the amine acylation prior to amide reduction). mp 115-118° C. (dec); 1H NMR (300 MHz, DMSO-d6) δ 8.65 (d), 8.10 (m), 7.95-7.15 (m), 6.50 (m), 3.60 (s), 3.25-2.95 (m), 2.95-2.40 (m), 2.40-1.70 (m), 1.35 (m), 0.9 (m); MS APCI, m/z=646 (M+).

Provenance & Evidence