Naratriptan → HCID 14392651, compound

Participants

Reaction Steps

Sodium hydride (60% w/w with paraffin; 124 mg) was added cautiously to a stirred solution the product of Example 1 in dry dimethylformamide (20 ml). The resultant mixture was stirred at room temperature under nitrogen for 0.25 h then a solution of methyl iodide (440 mg) in dry dimethylformamide (1 ml) was added in a stream. The mixture was stirred at room temperature for 2.5 h. The reaction mixture was quenched with water (3 ml), evaporated in vacuo and the residue was chromatographed on silica (150 g), eluting with dichloromethane, ethanol and ammonia (80:10:1) to give a gum. The gum was briefly triturated in diethyl ether and the title compound crystallised out as a powder (238 mg), m.p. 170°-172°.

Provenance & Evidence