Benzoyl chloride → HCID 18967541, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-amino-1-(1-methyl-3-piperidinyl)-naphthalene (0.203 g, 0.845 mmol, product of example 61) and triethylamine (0.141 mL, 1.01 mmol) in tetrahydrofuran (5 mL) was chilled to 0° C. and benzoyl chloride (0.118 mL, 1.01 mmol) was added. The mixture was warmed to room temperature and stirred overnight. The reaction was concentrated at reduced pressure and the residue was taken up in methylene chloride. The organic phase was extracted with 0.5N sodium hydroxide and brine, dried, concentrated onto silica gel and flash chromatographed (1×2 inches). Elution proceeded as follows: 50% ethyl acetate/hexane (225 mL), 75% ethyl acetate/hexane (150 mL) nil; 75% ethyl acetate/hexane (400 mL) and ethyl acetate (200 mL) 0.198 g of pink foam. This product was converted to an HCl salt in methanol, treated with activated carbon, and filtered. The filtrate was concentrated and triturated with ether to give 0.091 g (31%) of the title compound as an amorphous solid with a melting range of 140°-170° C. 1H NMR (DMSO d6) δ 10.59 (s, 1 H), 10.34 (br s, 1 H), 8.73 (s, 1H), 8.06 (d, J=7 Hz, 2 H), 7.94 (distorted t, J=10 Hz, 2 H), 7.82 (d, J=7 Hz, 1H), 7.63-7.53 (m, 3 H), 7.47-7.39 (m, 2 H), 3.78 (br t, J=12 Hz, 1 H), 3.56 (br t, J=11 Hz, 2 H), 3.05 (br s, 1 H), 2.83 (br s, 3 H), 2.15-1.97 (m0 2 H), 1.71 (br s, 1 H). HRMS m/e calculated for C23H24N2O; m/e 344.1883. Observed m/e 344.1886.

Provenance & Evidence