3-Ethoxy-2-propenoyl chloride → 1,6,7,8,9,10-Hexahydro-2h-azepino[3,2-g]quinolin-2-one

A solution of 2,3,4,5-tetrahydro-1H-1-benzazapin-8-amine (0.6 g, 3.4 mmol) and 3-ethoxyacryloyl chloride (0.45 g, 3.4 mmol) in CH2Cl2 (50 mL) and 3N NaOH (10 mL) was stirred for 1 h at ambient temperature. The reaction was partitioned between CH2Cl2 and water. The organic layer was concentrated and the remaining brown oil was dissolved in 70% aq. H2SO4 (20 mL) and heated gently (50° C.) for 2 h. The reaction was cooled and neutralized with aq. NH4OH and partitioned between water and EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The residue was dissolved in DMF (1 mL) and purified on a GILSON automated system affixed with a YMC COMBIFLASH 50 mm×20 mm reverse phase column eluted 5–95% CH3CN in water at 30 mL/min over 10.5 min to provide pure desired product. HRMS m/z (M+1) calcd 215.1179; found 215.1186.

1. customThe reaction was partitioned between CH2Cl2 and water
2. concentrationThe organic layer was concentrated
3. dissolutionthe remaining brown oil was dissolved in 70% aq. H2SO4 (20 mL)
4. temperatureThe reaction was cooled
5. custompartitioned between water and EtOAc
6. washThe organic layer was washed with brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. dissolutionThe residue was dissolved in DMF (1 mL)
11. custompurified on a GILSON automated system
12. washeluted 5–95% CH3CN in water at 30 mL/min over 10.5 min

ORD-Eintrag

ord-f67beddc9b33443db36a36f7388ba7e4

Quelldatensatz

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07196076B2