N-Methylbenzylamine → HCID 9827709, compound

Participants

Reaction Steps

(2-Chlorophenothiazin-10-yl)acetic acid (480 mg, 1.65 mmol) was dissolved in THF (10 mL). To this solution, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.58 g, 8.25 mmol), 1-hydroxybenzotriazole (220 mg, 1.65 mmol), and N-methyl benzyl amine (2.0 mL, 16.5 mmol) were added. The mixture was stirred at room temperature overnight and was then diluted with water and methylene chloride. The aqueous layer was made basic with sodium hydroxide (1N), and the layers were separated. The aqueous layer was extracted with methylene chloride. The organic layers were combined, washed with water and brine, dried (Na2SO4), filtered, and concentrated to provide a mixture of N-methyl benzyl amine and product (3.8 g). The residue was purified with a plug of SiO2. The product was recrystallized from hexane and ethyl acetate to provide N-benzyl-2-(2-chlorophenothiazin-10-yl)-N-methylacetamide as a white solid (258 mg, 40%).

Provenance & Evidence