2-(Dimethylamino)ethanol → HCID 70360573, compound

Participants

Reaction Steps

A mixture of 0.124 mole of sodium hydride (4.96 g of a 60% dispersion in oil; washed with hexane) and 13 g (0.146 mole) of 2-(N,N-dimethylamino)ethanol in 400 ml of dimethyl sulfoxide was stirred at room temperature and under an atmosophere of nitrogen for approximately 0.5 hr. To this solution was added 15.4 g (0.0519 mole) of N-[2-[(4-chlorophenyl)sulfonyl]ethyl]-1-methylethanamine hydrochloride [1:1] (from Preparation 23), and the mixture was stirred at 80°-100° C. for approximately 2 hr. The solvent was removed in vacuo, and the residue was partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride solution was dried over magnesium sulfate, and the solvent was removed in vacuo to give a liquid. This was treated with approximately 0.1 mole of maleic acid, and the resulting salt was recrystallized from methanol-diethyl ether to give 22.83 g (80.6%) of the product as a white crystalline solid, mp 177.5°-178.5° C.

Provenance & Evidence