Formaldehyde → 1-(2-Hydroxyethyl)-4-methylpiperazine

Participants

Reaction Steps

A mixture of 1-(2-hydroxyethyl)piperazine (10.0 g, 76.8 mmol), 37% aqueous formaldehyde solution (11.5 ml, 154 mmol), 10% palladium carbon catalyst (1.0 g) and methanol (100 ml) was stirred for 13 hr at room temperature in a hydrogen atmosphere. The reaction mixture was filtrated and the filtrate was concentrated. To the obtained residue was added 2N hydrochloric acid, and the mixture was washed with diethyl ether (200 ml). Sodium hydroxide (16 g) was added to the aqueous layer to make the layer alkaline, and the mixture was extracted with chloroform (4×200 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated to give the title compound (9.3 g, 84%) as a pale-yellow liquid.

Provenance & Evidence