Ethanol → 8-[(4-methylpiperazin-1-yl)methyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 501222

反応式

HRID 501222 の反応式
[NH:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1)N.[CH2:17](O)[CH3:18]>>[CH3:14][N:11]1[CH2:12][CH2:13][N:8]([CH2:7][C:6]2[CH:15]=[CH:16][C:3]3[NH:1][C:5]4[CH2:4][CH2:3][NH:1][CH2:17][C:18]=4[C:4]=3[CH:5]=2)[CH2:9][CH2:10]1

参加物

3

反応物 2

HCID 702EthanolHCID 684652221-(4-Hydrazinobenzyl)-4-methylpiperazine

生成物 1

HCID 684652088-[(4-methylpiperazin-1-yl)methyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

反応条件

温度
90 °C

実験手順

To a solution of 1-(4-hydrazinobenzyl)-4-methylpiperazine (3.4 g, 13.25 mmol) in ethanol (50 mL) were added piperidone. HCl (2.51 g, 18.55 mmol). The reaction temperature was raised to 90° C. and continued stirring for 2 hrs. The progress of the reaction was monitored by TLC and upon completion of the reaction the mixture was cooled to rt and HCl gas was bubbled through the reaction mixture at 0° C. After the reaction mixture was saturated with HCl, the temperature was raised to 90° C. again and continued stirring for 2 hrs. The ethanolic HCl was removed under reduced pressure and the pH of the reaction mixture was adjusted to 12.0 with 10% NaOH solution. The mixture was partitioned between 20% MeOH:DCM and water (35 mL) and the organic layer was separated, dried over Na2SO4 filtered and the solvent was removed under reduced pressure to give crude residue. Washing with ether gave 8-[(4-methylpiperazin-1-yl)methyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (1 g). 1H NMR (CD3OD, 200 MHz) δ: 7.31 (1H, s), 7.27 (1H, d, J=8.6 Hz), 7.06 (1H, d, J=8.6 Hz), 4.01 (2H, s), 3.60 (2H, s), 3.21 (8H, bm), 2.86 (4H, m), 2.28 (3H, s); m/e=285 (M+1).

後処理

  1. customThe progress of the reaction was monitored by TLC and upon completion of the reaction the mixture
  2. temperaturewas cooled to rt
  3. customHCl gas was bubbled through the reaction mixture at 0° C
  4. temperaturethe temperature was raised to 90° C. again
  5. stirringcontinued stirring for 2 hrs
  6. customThe ethanolic HCl was removed under reduced pressure
  7. customThe mixture was partitioned between 20% MeOH
  8. customDCM and water (35 mL) and the organic layer was separated
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. customthe solvent was removed under reduced pressure
  12. customto give crude residue
  13. washWashing with ether

出典と根拠

ORDレコード
ord-eefb087144624bffb523f11f392cef0f
出典データセット
uspto-grants-2010_08
特許番号
US07772245B2

関連ノート

読み込み中…