Triethylamine → HCID 68676087, compound

Temperature

120 °C

To a solution of (R)-3-cyclohexyl-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine (80 mg, 0.33 mmol) in 1,1,2,2-tetrachloroethane (2.0 ml), was added oxalyl chloride (46 mg, 0.36 mmol) with stirring under a stream of nitrogen. The mixture was heated at 120° C. for 1 hour. The mixture was cooled to room temperature and triethylamine (36 mg, 0.36 mmol) and N-ethylpiperazine (45 mg, 0.40 mmol) were added. The mixture was stirred at room temperature for 18 h then partitioned between dichloromethane and water. The aqueous layer was extracted with dichloromethane, and the combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The resulting brown oil was purified by flash chromatography using 5% (v/v) methanol in dichloromethane as eluent to yield the title compound as the free base. Hydrochloride salt formation was achieved by the addition of hydrogen chloride (2 M solution in diethyl ether, 0.5 ml) to a solution of the free base in diethyl ether (2 ml) and ethanol (1 ml). The solvent was removed in vacuo and the precipitate was dried to afford title compound (1:1 hydrochloride salt) as a solid (70 mg, 0.17 mmol).

1. temperatureThe mixture was cooled to room temperature
2. stirringThe mixture was stirred at room temperature for 18 h
3. customthen partitioned between dichloromethane and water
4. extractionThe aqueous layer was extracted with dichloromethane
5. washthe combined organic layers were washed with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. customThe resulting brown oil was purified by flash chromatography

ORD record

ord-1f43ac1250bd40a987e959d56530bcaf

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07772227B2