Toluene → HCID 59006376, compound

Participants

Reaction Steps

20% Phosgene in toluene (4.0 ml, 7.6 mmol) was diluted with ethyl acetate (20 ml, 205 mmol). 2-Fluoroaniline (0.600 ml, 6.2 mmol) was added to the mixture in one portion causing a white precipitate. Mixture was heated to reflux and held with stirring for 1 hour. Mixture was concentrated by roto-vap. Residue was dissolved in a small amount of dichloromethane. Resulting solution was added to a mixture of tert-butyl 4-(2,2-dimethoxyethylamino)piperidine-1-carboxylate (1.99 g, 6.9 mmol), dichloromethane (30 mL) and aqueous sodium bicarbonate (15 mL) while stirring vigorously. Reaction stirred at room temperature for 2 hours. Layers were separated and the aqueous phase was discarded. Material was washed twice with 1N hydrochloric acid and the aqueous phase was discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Title compound was obtained as yellow oil in 53% yield. MS (M−H)−=424.1.

Provenance & Evidence