Ethanol → Ethyl 3-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)propanoate

HRID 517834ノート

反応式

HRID 517834 の反応式
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]=1

参加物

5

反応物 4

HCID 702EthanolHCID 8471TriethylamineHCID 68320Ethyl 3-bromopropionateHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)

生成物 1

HCID 44159333Ethyl 3-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)propanoate

反応条件

温度
90 °C

実験手順

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.

後処理

  1. temperatureThe contents were cooled to 25° C.
  2. customevaporated to dryness
  3. customthe volatiles were removed under reduced pressure
  4. additionEthanol was added
  5. temperatureHeating
  6. concentrationThe contents were concentrated in vacuo
  7. additionby adding saturated aqueous NaHCO3
  8. extractionextracted with ethyl acetate
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. concentrationconcentrated
  11. customThe crude product was purified by chromatography on neutral alumina

出典と根拠

ORDレコード
ord-571628b8f8a947d693bc4c2aaba79d80
出典データセット
uspto-grants-2015_08
特許番号
US09115137B2

反応ノート

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