Phenylacetaldehyde → N-benzyl-4-methyl-2-(2-oxo-3-phenethylpiperidin-1-yl)thiazole-5-carboxamide

Participants

Reaction Steps

Following the procedure as described in Example 3, making variations as required to use 2-phenylacetaldehyde in place of cyclopropanecarbaldehyde to react with N-benzyl-4-methyl-2-(2-oxopiperidin-1-yl)thiazole-5-carboxamide in place of N-(4-fluorobenzyl)-4-methyl-2-(2-oxopyrrolidin-1-yl)thiazole-5-carboxamide, the title compound was obtained as a white solid in 24% yield: mp 124-126° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.46-7.09 (m, 10H), 5.98 (t, J=5.4 Hz, 1H), 4.55 (d, J=5.4 Hz, 2H), 4.29-4.20 (m, 1H), 4.07-4.04 (m, 1H), 2.83-2.66 (m, 2H), 2.64 (s, 3H), 2.61-2.48 (m, 1H), 2.41-2.26 (m, 1H), 2.17-2.01 (m, 2H), 1.96-1.76 (m, 2H), 1.74-1.58 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 172.8, 162.7, 156.9, 152.2, 141.3, 137.9, 128.8, 128.5, 128.4, 127.9, 127.6, 126.1, 119.1, 47.9, 44.1, 41.4, 33.3, 33.0, 25.7, 21.3, 17.4; MS (ES+) m/z 434.1 (M+1).

Provenance & Evidence