Trifluoroacetic acid → N-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-yl]-5-methoxy-isophthalamic acid methyl ester

Participants

Reaction Steps

In analogy to the procedure described in example 50k), 5-methoxy-N-piperidin-4-yl-isophthalamic acid methyl ester [prepared from 5-methoxy-isophthalic acid monomethyl ester (Synthetic Communications, 31(12), 1921-1926; 2001) by condensation with 4-amino-piperidine-carboxylic acid tert-butyl ester, using acid activation with 2-chloro-4,6-dimethoxy-1,3,5-triazine in analogy to the procedure described in example 50 h) followed by Boc cleavage with TFA in analogy to the procedure described in example 50i)] was reacted with 3,5-diethoxy-4-fluoro-benzaldehyde (example 50 g), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as colorless solid. MS: 489.3 (MH+).

Provenance & Evidence