Sodium Iodide → HCID 19737957, compound

Participants

Reaction Steps

The product from Step B (1.06 g, 5.62 mmol) was added to a suspension of NaH (0.97 g, 22.5 mmol) in DMF (19 mL) followed by chloroethylmorpholine hydrochloride (2.11 g, 11.21 mmol), and the mixture was warmed to 80° C. at which point NaI (1.1 g) was added and the mixture stirred for 20 min. The reaction mixture was diluted with water (80 mL) and extracted with methylene chloride (3×25 mL). The combined extracts were evaporated to a residue which was dissolved in ethyl acetate (80 mL) and the solution was extracted with 2N HCl (3×20 mL); this aqueous solution was adjusted to pH 7.5 with 2N NaOH and extracted with ethyl acetate (3×15 mL). The combined extracts were dried (MgSO4) and evaporated to a residue which was purified by column chromatography [silica, CH2Cl2 /CH3OH(3:1)] to give 1.68 g (98%) of the desired product as an oil.

Provenance & Evidence