Triethylamine → 6-chloro-N-[1-(hydroxymethyl)cyclohexyl]nicotinamide

Participants

Reaction Conditions

Reaction Steps

Triethylamine (2.2 ml, 16.12 mmol, 2 eq), hydroxybenzotriazole hydrate (0.217 g, 1.61 mmol, 0.2 eq), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.7 g, 8.87 mmol, 1.1 eq) are added to a cold (ice bath) solution of 6-chloronicotinic acid (1.27 g, 8.06 mmol, 1 eq) and (1-aminocyclohexyl)methanol (1.04 g, 8.06 mmol, 1 eq) in dichloromethane (80 ml), stirred 30 min at 0° C. and then at room temperature for 1 h. The organic layer is then washed with water, with a saturated solution of aqueous sodium hydrogenocarbonate and dried over magnesium sulfate. The solvent is finally removed to give 2.46 g of a yellow oil.

Provenance & Evidence