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

HRID 1400332ノート

反応式

HRID 1400332 の反応式
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

参加物

4

反応物 3

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

生成物 1

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

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f238c9c03a834e919f472a94c8800298
出典データセット
uspto-grants-2014_12
特許番号
US08906925B2

反応ノート

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