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

HRID 517834Notes

Reaction equation

HRID 517834 reaction equation
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

Participants

5

Reactant 4

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

Product 1

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

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-571628b8f8a947d693bc4c2aaba79d80
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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