Formaldehyde → HCID 11191429, compound

Participants

Reaction Steps

In methylene chloride (4.5 ml), 2-[[4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazin-1-yl]carbonyl]-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine hydrochloride (200 mg) was suspended, followed by the addition of triethylamine (125 μl), acetic acid (77.0 μl), formaldehyde (a 37% aqueous solution, 56.1 μl) and sodium triacetoxyborohydride (139 mg) at room temperature. The resulting mixture was stirred for 15 minutes. To the reaction mixture, a saturated aqueous solution (20 ml) of sodium bicarbonate and methylene chloride (10 ml) were added to separate the water layer. The resulting water layer was extracted with methylene chloride (2×10 ml). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue thus obtained was purified by chromatography on a silica gel column (25 g of silica gel, methylene chloride:methanol 10:1→7:1). The resulting solid was dissolved in a 1N aqueous hydrochloride in ethanol. After concentration of the resulting solution, water was added to the concentrate and the mixture was concentrated again, whereby the title compound (133 mg) was obtained as a white solid.

Provenance & Evidence