Triethylamine → HCID 18956267, compound

Participants

Reaction Steps

To a stirred solution of 1.0 g (3.25 mmols) of 2-(4-chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexanoic acid in 10 mL of tert-butanol was added 0.87 mL (3.25 mmols) of diphenylphosphorylazide followed by 0.33 mL of triethylamine. This mixture was heated to relux for 48 hours. The tert-butanol was removed under reduced pressure and the residue was taken up in 5% hydrochloric acid and washed with ethyl acetate. The acidic aqueous layer was made basic with concentrated ammonium hydroxide and extracted with ethyl acetate. Removal of solvents from the organic extract afforded 0.510 g (57%) of the amine as a viscous oil: 1H-NMR (CDCl3, Me4Si) 0.8-1.2 (t,J=6 Hz, CH2 --CH3), 1.2-1.7 (m), 1.7-2.2 (m), 2.0 (br s, --NH2), 4.6 (s, CH2 --N), 7.45 (s, phenyl H), 7.8 (s, CH=N), 8.0 ppm (s, CH=N);

Provenance & Evidence