1,1'-Thiocarbonyldiimidazole → HCID 19597355, compound

Participants

Reaction Steps

A solution of 4-phenyl-1-piperidinepropanamine (Example 5 intermediate) (3.2 g, 14.7 mmol) and 1,1'-thiocarbonyldiimidazole (2.8 g, 15.7 mmol) in MeCN (100 mL) was stirred for 2 h. The reaction mixture was chromatographed by vacuum filtration over silica (MeCN) to furnish 1-(3-isothiocyanatopropyl)-4-phenylpiperidine as an amber oil which crystallized upon standing (1.25 g, 33%). mp 50-55° C.; MS (ESI) m/z 261 (MH+); IR (KBr) 2113 cm-1. 1H NMR (CDCl3) δ 7.23 (m, 5H), 3.63 (t, 2 H, J=6.3 Hz), 3.08 (m, 2H), 2.55 (t, 2H, J=7.2 Hz), 2.50 (m, 1H), 2.15 (m, 2H), 1.95 (t, 2H, J=6.9 Hz), 1.86 (m, 4H). Anal. Calcd. for C15H20N2S.0.5 C2H3N: C, 66.28; H, 7.82; N, 12.08. Found: C, 66.68; H, 7.75; N, 12.22.

Provenance & Evidence