Dichloromethane → (3R)-3-((benzyloxy)methyl)-1-(2-thiophenylsulfonyl)piperazine

Participants

Reaction Conditions

Reaction Steps

A 1-L round-bottomed flask was charged with (R)-2-(benzyloxymethyl)piperazine dihydrochloride (55.5 g, 199 mmol) and 300 mL of CH2Cl2. After cooling to 0° C., triethylamine (111 mL, 795 mmol) and 2-thiophenesulfonyl chloride (36.3 g, 199 mmol, Sigma-Aldrich, St. Louis, Mo.) were added. This mixture was stirred at 0° C. for 30 min and then diluted with water. The organics were separated, dried (MgSO4), filtered and concentrated to give a brown oil. Purification via column chromatography on silica gel (25 to 100% EtOAc in hexanes) gave (3R)-3-((benzyloxy)methyl)-1-(2-thiophenylsulfonyl)piperazine (47.8 g) as a light-brown solid.

Provenance & Evidence