Piperidine → HCID 54721731, compound

Participants

Reaction Steps

The title compound was prepared as described in example 41 using the following: 5,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one (0.250 g, 0.850 mmol), t-butanol (3.5 mL), n-bromosuccinimide (0.151 g, 0.85 mmol), CH2Cl2 (6.0 mL), 1-isopropyltetrahydropyrimidine-2-thione (0.270 g, 1.70 mmol, prepared by the method described by A. F. McKay et al., J. Am. Chem. Soc., 78: 1618 (1956)), piperidine (0.084 mL, 0.85 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 1/1 CH2Cl2 /ethyl acetate to 2/14/1 ethyl acetate/CH2Cl2 /methanol) to provide a solid which was redissolved in CH2Cl2, filtered through a fiberglass filter, and the solvent removed in vacuo to provide the title compound (0.356 g, m.p. 103°-105° C). 1H NMR (400 MHz, DMSO-d6) δ 7.440-7.371 (m, 4 H), 7.296 (t, 1 H, J=7 Hz), 7.233 (t, 2 H, J=7 Hz), 7.139 (t, 1 H, J=7 Hz), 7.077 (d, 2 H, J=7 Hz), 6.515 (bs, 1 H), 4.365-4.300 (m, 1 H), 3.335-3.308 (m, 2 H), 3.024 -2.924 (m, 4 H), 2.624-2.548 (m, 1 H), 2.341-2.265 (m, 1 H), 2.156-2.061 (m, 2 H), 1.763-1.737 (m, 2 H), 1.201-1.180 (m, 6 H).

Provenance & Evidence