Sodium hydride → HCID 17875246, compound

Participants

Reaction Steps

To an ice-cooled solution of 3-hydroxy-N-Boc,N-methyl phenethylamine (5.0 g, 19.9 mmol) in dry acetonitrile (65 ml) was added under nitrogen, N-methyl,N-n-propyl carbamoyl chloride (4.66 g, 34.43 mmol), followed by the portionwise addition of NaH (60% disp. in oil, 1.03 g, 25.87 mmol). The reaction mixture was stirred at RT under nitrogen for 6 hrs and evaporated to dryness in-vacuo. Water (200 ml) was added, the pH was adjusted to ˜9 and the aqueous layer was extracted with ether (4×100 ml). The combined ether layer was washed with NaOH solution (pH 9.5), water (150 ml), dried (Na2SO4) and evaporated to dryness in-vacuo to give an oil which was purified by column chromatography (hexane:EtOAc 2:1), affording 6.0 g (86%) of the title compound as a yellow oil.

Provenance & Evidence