Ammonia → HCID 19831295, compound

Participants

Reaction Steps

To a solution of (±) N-[(1-ethyl-2-pyrrolidinyl)methyl]-3-methoxy-4,5-dimethylthiophene-2-carboxamide, fumarate (3 g) in dilute sulphuric acid (100 ml concentrated sulphuric acid in 500 ml water) was added ammonium cerium nitrate (17.56 g) in one portion. After stirring at room temperature for 0.5 hours and then cooling to 0° C., 0.88 ammonia solution (235 ml) was added dropwise to give a neutral solution. This was extracted several times with dichloromethane, the organic extracts combined and washed with water, dried over magnesium sulphate and the solvent removed in vacuo to give a light brown oil. Column chromatography on silica eluting with 10% methanol in dichloromethane gave the pure free base of the title compound, fumarate salt, m.p. 122°-123° C. (ex ethyl acetate-ethanol as recrystallising solvent).

Provenance & Evidence