Diisopropylamine → HCID 21808099, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyl lithium (8.27 ml, 1.6 M in hexanes, 13.23 mmol) was added to diisopropylamine (13.36 mmol, 1.95 ml) in dry THF (10 ml) at −78° C. and stirred for 0.5 h (to make lithium diisopropylamine, LDA). The mixture was warmed to room temp. for 20 min, then cooled down to −78° C. again. Ethyl isonicotinate (1.00 g, 6.62 mmol, 0.91 ml) was dissolved in dry THF (30 mL) and cooled to −78° C. under an atmosphere of argon. The freshly prepared LDA was added to the ethyl isonicotinate solution dropwise. The mixture was left to stir for 1 h, then allowed to warm to room temperature for 0.5 h. The reaction mixture was cooled to −78° C. again and 1,2-dibromotetrafluoroethane (6.62 mmol, 0.79 ml) in THF (10 mL) was added slowly. The reaction was stirred at −78° C. for 1 h, then stirred at room temp. overnight. Water (40 ml) was added. The organic layer was separated, and the aqueous layer was washed with CHCl3 (3×100 ml). The combined organic solutions were dried (Na2SO4) and the solvent removed to give the crude compound. The crude compound was columned [8:2 benzene:acetone as eluant], to give diisopropyl isonicotinamide [Registry No. 77924-05-1]. 1H NMR (300 MHz, CDCl3) 8.66 (2H, d, J 6 Hz), 7.19 (2H, d, J 6 Hz), 3.69 (1H, bs), 3.55 (1H, bs), 1.54 (6H, bs) and 1.16 (6H, bs).

Provenance & Evidence