Piperidine → HCID 11567221, compound

Participants

Reaction Steps

4-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbaldehyde (272 mg, 0.86 mmol), piperidine (0.161 mL, 1.63 mmol), absolute ethanol (11 mL), activated 4 Å molecular sieves, titanium (IV) isopropoxide (1.205 mL, 4.28 mmol) and STAB (1.54 g, 7.28 mmol) were reacted in accordance with the general procedure D. The isolated waxy solid was purified by column chromatography on silica eluting with a gradient of DCM:MeOH:NH3 (from 99:0:1 to 90:9:1) to give the title compound (97.4 mg, 25%). 1H NMR (400 MHz, CDCl3) δ 7.21 (d, 2H), 6.85 (d, 2H), 4.02 (t, 2H), 3.77-3.72 (m, 2H), 3.54-3.48 (t, 2H), 2.63 (t, 2H), 2.53 (m, 4H), 2.29 (s, 2H), 2.13-1.87 (m, 10H), 1.79 (quint, 4H), 1.41-1.36 (m, 4H), 1.30-1.26 (m, 2H).

Provenance & Evidence