Indole-5-carbonitrile, 3-(2-dimethylaminoethyl)- → 2-(5-(Aminomethyl)-1H-indol-3-yl)-N,N-dimethylethanamine

HRID 2223801

反応式

HRID 2223801 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([CH3:22])[CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=2)[NH:13][CH:12]=1>>[NH2:21][CH2:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH2:10][CH2:9][N:8]([CH3:7])[CH3:22]

参加物

3

反応物 2

HCID 28511Indole-5-carbonitrile, 3-(2-dimethylaminoethyl)-HCID 21226445Aluminium lithium hydride

生成物 1

HCID 574744522-(5-(Aminomethyl)-1H-indol-3-yl)-N,N-dimethylethanamine

実験手順

Lithium aluminium hydride (40.0 mg, 1.055 mmol, 1.5 equivalents) was placed in an argon purged oven dried flask fitted with a stirbar and condenser. Anhydrous diethylether (5 mL) was added and stirring begun. 3-(2-Dimethylamino-ethyl)-1H-indole-5-carbonitrile (57) (150.0 mg, 0.703 mmol, 1.0 equivalent) was dissolved in a separate dry flask in a mixture of anhydrous diethylether (5 mL) and anhydrous tetrahydrofuran (5 mL) and this solution added dropwise to the solution of lithium aluminium hydride and the resulting mixture heated to reflux. After 30 minutes the reaction was cooled to room temperature and quenched with distilled water (50 μL), aqueous 3N sodium hydroxide solution (75 μL) and distilled water (150 μL) sequentially. The solution was filtered and concentrated. The residue was purified via silica gel column chromatography (10-15-20% 2M NH3 in methanol/90-85-80% dichloromethane) to provide 2-(5-(aminomethyl)-1H-indol-3-yl)-N,N-dimethylethanamine (58) as a pale yellow residue (73 mg, 47.8% yield). 1H NMR (DMSO) δ: 2.21 (s, 6H), 2.53 (m, 2H), 2.78 (t, 2H), 3.79 (s, 2H), 7.02-7.05 (d, 1H), 7.09 (s, 1H), 7.24 (d, 1H), 7.44 (s, 1H), 10.66 (br s, 1H). MS: 218 (M+1), 201 (M+1—NH3).

後処理

  1. customdried flask
  2. customfitted with a stirbar and condenser
  3. additionAnhydrous diethylether (5 mL) was added
  4. customdry flask
  5. additionin a mixture of anhydrous diethylether (5 mL) and anhydrous tetrahydrofuran (5 mL)
  6. additionthis solution added dropwise to the solution of lithium aluminium hydride
  7. temperaturethe resulting mixture heated to reflux
  8. customquenched with distilled water (50 μL), aqueous 3N sodium hydroxide solution (75 μL)
  9. distillationdistilled water (150 μL) sequentially
  10. filtrationThe solution was filtered
  11. concentrationconcentrated
  12. customThe residue was purified via silica gel column chromatography (10-15-20% 2M NH3 in methanol/90-85-80% dichloromethane)

出典と根拠

ORDレコード
ord-027d16dcaf794d0096cc8bb856d10805
出典データセット
uspto-grants-2008_05
特許番号
US07375219B2

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