Aluminium lithium hydride → [3-(7-Methoxy-1H-Indol-4-yl)-3-phenyl-propyl]-methyl-amine

HRID 1716662ノート

反応式

HRID 1716662 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:12]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][C:14]([NH:16][CH3:17])=O)=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:12]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:14][NH:16][CH3:17])=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydride2 回HCID 598317653-(7-Methoxy-1H-Indol-4-yl)-N-methyl-3-phenyl-propionamide

生成物 1

HCID 59831752[3-(7-Methoxy-1H-Indol-4-yl)-3-phenyl-propyl]-methyl-amine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

To a 0° C. solution of 3-(7-methoxy-1H-Indol-4-yl)-N-methyl-3-phenyl-propionamide LV (0.315 mmol) in THF (3 ml) was added a suspension of LiAlH4 (46.6 mg, 1.26 mmol) in THF (4 ml). The resulting mixture was stirred at 0° C. for 5 minutes, at reflux for 5 hours, then cooled to room temperature, and additional suspension of LiAlH4 (46.6 mg, 1.26 mmol) in THF (4 ml) was added. The reaction was refluxed for additional 45 minutes, cooled to 0° C. and freshly ground Na2SO4.10H2O (1 g) was added. The mixture was stirred at room temperature over the weekend. The solid was filtered and washed with EtOAc. The filtrate was concentrated and purified via flash chromatography (DCM/MeOH/NH4OH) to provide the amine compound LVI as a yellow film (37 mg). The free amine was dissolved in Et2O (3 ml), cooled to 0° C., and HCl (1 M in Et2O, 126 μl) was added. The precipitate was filtered affording the hydrochloride salt of [3-(7-Methoxy-1H-Indol-4-yl)-3-phenyl-propyl]-methyl-amine LVI as an off-white hygroscopic powder. MS (M+H)=295.

後処理

  1. temperatureat reflux for 5 hours
  2. temperaturecooled to room temperature
  3. additionwas added
  4. temperatureThe reaction was refluxed for additional 45 minutes
  5. temperaturecooled to 0° C.
  6. stirringThe mixture was stirred at room temperature over the weekend
  7. filtrationThe solid was filtered
  8. washwashed with EtOAc
  9. concentrationThe filtrate was concentrated
  10. custompurified via flash chromatography (DCM/MeOH/NH4OH)

出典と根拠

ORDレコード
ord-e9cc9958adfc4eb59347e4b5b25ca3a1
出典データセット
uspto-grants-2010_09
特許番号
US07803830B2

反応ノート

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