1-Bromopropane → HCID 20230785, compound

Participants

Reaction Steps

A slurry of NaH (0.68 g, 50% in oil, 14.1 mmole, washed 3 times with hexane) and 68 mL dry DMF was stirred under N2 at room temperature as a solution of the compound of example 5 (free base) (3.0 g, 12.9 mmole) in 20 mL dry DMF was added dropwise. The reaction mixture was stirred for 1.5 hr. at room temperature, then 1-bromopropane (1.3 mL, 14.1 mmole) was added dropwise. The reaction mixture was stirred for 1 hr at room temperature, and for 18 hrs. at 30°-35° C. The reaction mixture was evaporated to dryness, water was added and the solution was extracted 3 times with CH2Cl2. The combined CH2Cl2 layers were washed with water, brine, dried (MgSO4), filtered, evaporated, and converted to the HCl salt to yield 2.0 g (50%) gray glass; M+ 246.

Provenance & Evidence