Triethylamine → HCID 14570090, compound

Participants

Reaction Steps

To an ice-cooled solution of 0.508 g 1.85 mmol) of 3,4-diphenylbenzoic acid in 10 mL of anhydrous DMF was added 0.44 mL of diphenylphosphoryl azide with stirring. Triethylamine (0.28 mL) was then added and stirring at 3° C. 0 was continued for 1 hour. 3-pyridinebutanamine (0.309 g) was added and stirring was continue for 30 minutes at 3° C. and for 17 hours at room temperature. The solvent was removed under the oil pump vacuum and ethyl acetate was added to the residue. The solution was washed with aqueous 5% sodium bicarbonate. dried (MgSO4) and concentrated in vacuo. The residual oil was chromatographed on 50 g of silica gel, eluting with methylene chloride-methanol-conc.ammonium hydroxide (95:5:0.05). The pure fractions were combined and lyophilized from benzene to yield a 0.708 g of 3,4-Diphenyl-N-[4-(3-pyridinyl)butyl]benzamide 0.25 molar hydrate as a colorless foam.

Provenance & Evidence