Diethylammonium chloride → HCID 9868790, compound

Participants

Reaction Steps

To a stirring suspension of diethyl amine hydrochloride (986 mg, 9.01 mmol) in 1,2-dicloroethane (25 mL) at 0° C. was added a 2.0 M solution of AlMe3 (4.5 mL, 9.01 mmol) dropwise. The resulting mixture stirred at room temperature for 1 hour. (2-[1-Benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-pyrimidine-5-carboxylic acid methyl ester (750 mg, 1.80 mmol) was added in one portion and the mixture was heated to 85° C. for 16 hours. The reaction was slowly poured into a saturated solution of Rochelle salts (50 mL) and diluted with CH2Cl2 (50 mL). The layers were separated, the aqueous layer was extracted with CH2Cl2 (3×30 mL) and the combined organic layers were dried and concentrated. The crude material was filtered through a plug of silica gel with 5% MeOH/CHCl3, and the resulting solution was concentrated to yield 815 mg (99% yield) of the desired amide. 1HNMR (400 MHz, CDCl3) δ 8.72 (s, 2H), 7.29-7.14 (comp, 6H), 6.97-6.95 (comp, 2H), 6.68-6.66 (comp, 1H), 3.73 (s, 3H), 3.54-3.52 (comp, 2H), 3.39 (s, 2H), 3.27-3.25 (comp, 2H), 2.98-2.95 (comp, 2H), 2.77-2.74 (comp, 2H), 2.34-2.31 (comp, 2H), 2.16-2.02 (comp, 2H), 1.26-1.17 (comp, 6H); MS (M+1) 459.2.

Provenance & Evidence