Acetic Acid → 8-Benzyl-1-(3-methyl-phenyl)-1,3,8-triazaspiro[4,5]dec-2-en-4-one

Participants

Reaction Steps

To a mixture of 1-benzyl-4-(3-methylphenylamino)-isonipecotamide (4.3 g, 13.5 mmol) and glacial acetic acid (1.0 mL) in toluene (20 mL) heated under reflux, triethyl orthoformate (2.0 g, 13.5 mmol) was added over a period of 3 h using a syringe pump. The resultant mixture was refluxed for 38 h., and treated with a mixture of concentrated ammonium hydroxide (1.3 mL) and water (3.4 mL). The organic extract was isolated, washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was subjected to column chromatography on silica gel eluting with 5% methanol in chloroform. Collection and concentration of appropriate fractions provided the title compound.

Provenance & Evidence