Hydrochloric Acid → Methyl 2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxylate

HRID 1400332Notes

Reaction equation

HRID 1400332 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([NH:11]N)=[CH:7][CH:6]=1.Cl.[CH3:15][N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.Cl>>[CH3:15][N:16]1[CH2:21][CH2:20][C:19]2[NH:11][C:8]3[CH:7]=[CH:6][C:5]([C:4]([O:3][CH3:2])=[O:13])=[CH:10][C:9]=3[C:18]=2[CH2:17]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 2788448Methyl 4-hydrazinobenzoate hydrochlorideHCID 122100571-Methylpiperidin-4-one hydrochloride

Product 1

HCID 1070332Methyl 2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxylate

Conditions

Temperature
100 °C

Procedure

Methyl-4-hydrazinylbenzoate hydrochloride (1 equiv.) and 1-methylpiperidin-4-one HCl (0.76-1.4 equiv.) are taken aqueous HCl and heated at 100° C. overnight (the product was detected by LCMS). The reaction mixture is concentrated and refluxed (90° C.) in methanolic HCl overnight (product was detected by LCMS and TLC). The reaction mixture is concentrated and basified with aqueous NaHCO3 solution and extracted with EtOAc. The crude product is crystallized in DCM and ether and hexane.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. temperaturerefluxed (90° C.) in methanolic HCl overnight (product was detected by LCMS and TLC)
  3. concentrationThe reaction mixture is concentrated
  4. extractionextracted with EtOAc
  5. customThe crude product is crystallized in DCM

Sources & evidence

ORD record
ord-f238c9c03a834e919f472a94c8800298
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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