2-(Dimethylamino)ethanol → HCID 46233349, compound

Participants

Reaction Conditions

Reaction Steps

2-dimethylaminoethanol (2 mL, 20 mmol) was added at rt to a suspension of NaH (oil was not removed) in dry DMF (3 mL). The mixture was stirred at rt for 2 hours and 1 h at 60° C. Then commercial 2,6-dibromopyridine (6.16 g, 26 mmol, 1.3 eq) was added at rt and the whole was stirred at rt overnight. The crude mixture was dissolved in some Et2O and was extracted with 2 portions of citric acid 30%. Combined aqueous phases were washed with 2 portions of Et2O. The aqueous phase was basified with NaOH 5N at 0° C. and was extracted with 3 portions of Et2O. Combined organic phases was dried over MgSO4, filtrated and evaporated. As some DMF remained, HCl in Et2O was added. The solvents were evaporated and the resulting solid was put at the pump for 4 hours. It was dissolved in H2O and basified with NaOH 5 M. The desired product (the base) was extracted with 3 portions of Et2O. Combined organic layers were dried over MgSO4, filtrated and evaporated to give the desired product (XXIII), N-{2-[(6-bromo-2-pyridinyl)oxy]ethyl}-N,N-dimethylamine (4.4309 g, 18.076 mmol, 90.4%).

Provenance & Evidence