Acetyl chloride → HCID 67131297, compound

Participants

Reaction Steps

To a solution of 1-benzyl-2′,3′-dihydro-1′H-spiro[piperidine-4,4′-quinoline] 1ad (4.5 g, 15.4 mmol) in dry CH2Cl2 (35 mL) was added NaHCO3 (6.47 g, 77 mmol) at room temperature. Then acetyl chloride (1.2 g, 15.4 mmol) was added dropwise at ambient temperature. The mixture was stirred for 2 hours at room temperature. After filtration, the filtrate was washed with brine, dried over Na2SO4 and evaporated under reduced pressure to give a white solid, which was washed with ether and filtered to afford the pure product 1-(1-benzyl-2′,3′-dihydro-1′H-spiro[piperidine-4,4′-quinoline]-1′-yl)ethanone 1ae (not shown). The solid (5.2 g, 15.6 mmol) was dissolved in MeOH (50 mL), then Pd(OH)2/C (0.25 g) was added under Ar. The suspension was hydrogenated under H2 (50 psi) at 50-55° C. overnight. After cooling and filtration, the filtrate was evaporated under reduced pressure to give 1-(2′,3′-dihydro-1′H-spiro[piperidine-4,4′-quinoline]-1′-yl)ethanone 1ae (3.12 g, 83%, two steps). 1H NMR (CDCl3, 300 MHz) δ 7.46-7.49 (m, 2H), 7.21-7.26 (m, 3H), 3.82 (t, J=5.7 Hz, 2H), 3.38 (d, J=12.9 Hz, 2H), 3.08-3.16 (m, 2H), 2.38-2.48 (m, 2H), 2.24 (s, 3H), 1.97 (t, J=6.0 Hz, 2H), 1.77 (d, J=14.7 Hz, 2H). MS (ESI) m/z (M+H+) 245.2.

Provenance & Evidence