Triethylamine → N-(4-aminobenzyl)pivalamide

Participants

Reaction Steps

To a 0° C. solution of 2.5 ml (22 mmol) 4-aminobenzylamine in 100 mL CH2Cl2 was added 3 mL (22 mmol) triethylamine and 2.7 mL (22 mmol) pivaloyl chloride slowly by syringe over 5 min. and the reaction mixture was warmed to room temperature and stirred 1 hour. Additional portions of. triethylamine (0.4 ml )and pivaloyl chloride (0.4 ml) were added and the reaction mixture was allowed to stir 16 hours. The reaction mixture was then diluted with 400 mL EtOAc, washed with 400 mL each of, saturated aqueous NaHCO3, water, and brine, then dried over Na2SO4, filtered and concentrated. The residue was purified by washing with 100 mL EtOAc, and extracting this wash with 2×100 mL 1N HCl. The combined aqueous extracts were brought to pH>10 with 6M NaOH and extracted 3×100 mL EtOAc. The combined EtOAc extracts were then dried over Na2SO4, filtered and concentrated to give 2.5 g N-(4-amino-benzyl)-2,2-dimethyl-propionamide as a off-white solid. 1H NMR (300 mHz, CDCl3) δ 7.15 (d, 2H); 6.65 (d, 2H); 5.75 (b s, 1H); 4.30 (d, 2H); 3.65 (b s, 2H); 1.20 (s, 9H).

Provenance & Evidence