Benzylamine → 1-Benzyl-3-(4-chloro-phenyl)-5-methyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

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Reaction Steps

1-Benzyl-3-(4-chloro-phenyl)-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid ethyl ester. To a stirred solution of 3.0 g of 4-oxo-piperidine-1-carboxylic acid ethyl ester in benzene (35 mL) was added 1.91 mL of benzylamine. The mixture was heated at reflux for 24 h using a Dean-Stark apparatus. The solvent was removed to give a pale yellow oil. A portion of the crude product (0.50 g) was dissolved in toluene (4 mL) and 0.35 g of 1-chloro-4-(2-nitro-vinyl)-benzene was added, followed by 0.7 g of 4 Å molecular sieves. The resulting mixture was stirred for 12 h at RT. The mixture was then filtered through diatomaceous earth and the filtrate was washed with satd. aq. NH4Cl (3×). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. Chromatography on SiO2 (8% EtOAc/hexanes) afforded 0.25 g the title compound. TLC (SiO2, 25% EtOAc/hexanes): Rf=0.34. MS (ESI): exact mass calculated for C23H23ClN2O2, 394.14; found, m/z 395.2 [M+H]+, 397.2 [M+H]+, 417.1 [M+Na]+.

Provenance & Evidence