Diisopropylethylamine → HCID 58504140, compound

Participants

Reaction Steps

1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (2.26 g) and diisopropylethylamine (2.05 mL) were added to a room temperature solution of 4-chloro-3-methoxybenzoic acid (2.00 g) and 1-hydroxybenzotriazole hydrate (1.81 g) in dichloromethane (53 mL). After the reaction was stirred for five minutes, tert-butyl 4-(aminomethyl)piperidine-1-carboxylate (2.53 g) was added and the mixture was stirred overnight. The reaction was then partitioned between 1 N hydrochloric acid and dichloromethane. The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated and purified by column chromatography on silica gel (dichloromethane:methanol=19:1). The resulting residue was triturated in diethyl ether and the solids were collected by filtration to obtain the title compound (3.56 g) having the following physical data. 1H NMR (DMSO-d6): δ 8.60 (t, J=5.7 Hz, 1H), 7.61-7.39 (m, 3H), 3.91 (m, 5H), 3.15 (t, J=6.0 Hz, 2H), 2.81-2.62 (m, 2H), 1.72-1.51 (m, 3H), 1.39 (s, 9H), 1.12-0.92 (m, 2H)+;

Provenance & Evidence