Formaldehyde → HCID 19095288, compound

Participants

Reaction Steps

Crude 1-(2-aminoethyl)-2-phenylpyrrole (0.3 g) was dissolved in 5 ml of acetic acid under argon and treated with 0.1 ml of a 36.5% aqueous formaldehyde solution. The reaction mixture was stirred at room temperature for 64 hours and subsequently concentrated in a vacuum. The residue was stirred briefly with 50 ml of methylene chloride and 20 ml of 10% ammonia solution. The phases were separated, the organic phase was dried with MgSO4 and freed from solvent. The residue, 0.4 g of yellow oil, was chromatographed on 70 g of silica gel with methylene chloride/methanol (49:1) as the eluent. The product, 0.3 g of yellow oil, was taken up in a 20-fold amount of ethanol and treated with 2 equivalents of a saturated solution of fumaric acid in ethanol. The separated crystals were recrystallized from ethanol. There was obtained 0.2 g (40%) of 1,2,3,4-tetrahydro-6-phenylpyrrolo[1,2-a]pyrazine fumarate (1:1); m.pt.: 182°- 184° C. (dec.).

Provenance & Evidence