Ethanol → HCID 68968162, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-4-(3-piperidin-1-ylpropoxy)benzonitrile (D26) (6.29 g) with aqueous 1M sodium hydroxide (45.2 ml) in ethanol (60 ml) was heated at reflux for 72 h. The reaction mixture was then evaporated to remove ethanol and the aqueous solution treated with excess conc. hydrochloric acid and heated at 120° C. for 2 h. The reaction mixture was then cooled to 5° C. and filtered. The filter cake was washed with a small volume of water and then acetone followed by drying at 65° C. under high vacuum overnight to give the title compound (D27) as a pale brown powder (6.48 g). MS electrospray (+ion) 298/230 (MH+). 1H NMR δ (DMSO-d6): 13.05 (1H, s), 10.85 (1H, s), 7.89 (1H, d, J=8.7 Hz), 7.10 (1H, s), 7.02 (1H, d, J=8.7 Hz), 4.16 (2H, t, J=6.0 Hz), 3.40 (2H, m), 3.13 (2H, m), 2.88 (2H, m), 2.23 (2H, m), 1.94-1.35 (6H, m).

Provenance & Evidence