HCID 20289414, compound → HCID 20289413, compound

Participants

Reaction Steps

To a solution of 10.86 g of 2-[[4-butyl-6-[(phenylmethoxy)methyl]-2-morpholinyl]methoxy]-N,N-dipropylacetamide (0.025 mole) in 125 ml of glacial acetic acid is added 4.0 g of 10% Pd/C and the mixture is hydrogenated at 50 psi at 60° over a period of 28 hours (debenzylation taking up 94% of the calculated theory). The mixture is cooled to room temperature and the Pd/C removed via filtration through a pad of "celite" filter aid. The acetic acid is removed in vacuo yielding a pale yellow oil. The oil is taken up in 200 ml of chloroform and washed with 100 ml of saturated NaHCO3 solution. The CHCl3 layer is separated, dried over anhydrous Na2SO4 and then the CHCl3 is removed in vacuo yielding 8.2 g (95%) of crude product as a dark brown oil. The oil is chromatographed on 150 g of neutral Alumina III to give 0.5 g of forerun (eluted with 100 ml of chloroform) and 7.6 g (88%) of the desired product (eluted with 400 ml of chloroform and 200 ml of 2% methanolic chloroform). The 7.6 g of product is dried in vacuo to give the desired product, a dense yellow-orange oil.

Provenance & Evidence