Water → HCID 20289414, compound

Participants

Reaction Steps

A mixture of 16.2 g of 4-butyl-6-[(phenylmethoxy)methyl]-2-morpholinemethanol (0.055 mole) and 9.81 g of 2-chloro-N,N-dipropylacetamide (0.055 mole) are dissolved in 200 ml of dry dimethyl sulfoxide and the mixture stirred at room temperature under nitrogen. Slowly, 1.0 g of sodium hydroxide (0.04 mole) is added to the dimethyl sulfoxide mixture and the reaction allowed to stir at ambient temperature (23°). After stirring for 10 minutes an exothermic reaction begins to take place and an ice-bath is used to maintain the reaction temperature below 30°. After stirring for 1 hour the ice-bath is removed and the reaction allowed to stir at room temperature for 18 hours. The excess NaH is destroyed by adding 5 ml of methanol and the entire reaction mixture is then poured into 400 ml of water. The product is extracted with 3×125 ml portions of chloroform. The CHCl3 extracts are combined and washed with 4×300 ml portions of water. The CHCl3 layer is separated, dried over anhydrous Na2SO4, and the CHCl3 removed in vacuo yielding 22.4 g (94%) of the title compound as a yellow oil. The resulting oil is purified on a neutral Alumina III column (500 g), 40% chloroform/hexane yielding 12.9 g (54%) of product as a pale yellow oil. The 12.9 g of product are dried in vacuo (80° @0.2 mm) to give the desired product.

Provenance & Evidence