Ethanol → Ethyl 3-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)propanoate
반응식
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.Br[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].[CH2:19]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])C.[CH2:26](O)C>>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]2[N:9]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:26]3[CH2:23][CH2:22][N:21]([CH3:19])[CH2:24][C:25]=3[C:5]=2[CH:4]=1참가 물질
반응 조건
- 온도
- 90 °C
실험 절차
4-Chlorophenylhydrazine hydrochloride, ethyl 3-bromopropionate and triethylamine in ethanol were stirred at 25° C. for 1 h after which the contents were heated at 90° C. for 3 h. The contents were cooled to 25° C. and evaporated to dryness. The residue was acidified with ethanolic HCl and the volatiles were removed under reduced pressure. Ethanol was added followed by N-methyl-4-piperidone hydrochloride. Heating was continued at 90° C. for 16 h. The contents were concentrated in vacuo, basified by adding saturated aqueous NaHCO3, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The crude product was purified by chromatography on neutral alumina using methanol-dichloromethane gradient to obtain ethyl 3-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)propanoate.
후처리
- temperatureThe contents were cooled to 25° C.
- customevaporated to dryness
- customthe volatiles were removed under reduced pressure
- additionEthanol was added
- temperatureHeating
- concentrationThe contents were concentrated in vacuo
- additionby adding saturated aqueous NaHCO3
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated
- customThe crude product was purified by chromatography on neutral alumina
출처 및 근거
- ORD 기록
- ord-571628b8f8a947d693bc4c2aaba79d80
- 출처 데이터셋
- uspto-grants-2015_08
- 특허 번호
- US09115137B2
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