Sodium Bicarbonate → Theophylline

Participants

Reaction Steps

To a solution of 502 mg (0.86 mmol) of the theophylline derivative in 8 ml of methanol was added, under argon atmosphere, 360 mg (1.90 mmol) of p-toluenesulfonic acid monohydrate, and the mixture was heated under reflux for 4 hours. The reaction mixture was cooled to room temperature, adjusted to a pH value of 10 by the addition of a saturated aqueous solution of sodium hydrogencarbonate, and then extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The residue (540 mg) was subjected to silica gel column chromatography, eluted with chloroform-methanol (50:1), to give 225 mg (0.45 mmol) of 7-[2-[4-[5-(3-methoxy-4-hydroxyphenyl)-2,4]-pentadienoyl]piperazin-1-yl]ethyl]theophylline.

Provenance & Evidence