Ethanol → Tetrabenazine

HRID 38313

反応式

HRID 38313 の反応式
[I-].[C:2]([CH:5]([CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:6][N+:7]([CH3:10])([CH3:9])C)(=[O:4])[CH3:3].[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:26]=1[O:27][CH3:28])C=NC[CH2:20]2.C(O)C.O>ClCCl>[CH2:11]([CH:5]1[CH2:6][N:7]2[CH2:9][CH2:20][C:19]3[C:24]([CH:10]2[CH2:3][C:2]1=[O:4])=[CH:25][C:26]([O:27][CH3:28])=[C:17]([O:16][CH3:15])[CH:18]=3)[CH:12]([CH3:13])[CH3:14]

参加物

6

反応物 4

HCID 702EthanolHCID 962WaterHCID 300583,4-Dihydro-6,7-dimethoxyisoquinolineHCID 86641883(2-Acetyl-4-methylpentyl)trimethylammonium Iodide

生成物 1

HCID 6018Tetrabenazine収率 37.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(2-Acetyl-4-methyl-pentyl)-trimethyl-ammonium iodide (800 mg, 2.55 mmol, 1.00 equiv) was added to a solution of 6,7-dimethoxy-3,4-dihydroisoquinoline (100 mg, 2.62 mmol, 1.00 equiv) and ethanol (10 mL). The resulting solution was heated at reflux for about 5 hours, and then water (20 mL) was added. Following standard extractive workup with dichloromethane (3×50 mL), the crude residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether (1:4)) to afford the title compound as a white solid (300 mg, yield=36%). 1H NMR (300 MHz, CDCl3), δ 6.63 (s, 1H), 6.55 (s, 1H), 3.89 (s, 3H), 3.83 (s, 3H), 3.55 (s, 1H), 3.22-3.28 (m, 1H), 2.94-3.14 (m, 4H), 2.31-2.65 (m, 4H), 1.73-1.81 (t, 1H, J=11.4), 1.33-1.39 (m, 1H), 0.996-1.067 (t, 1H, J=10.5), 0.79-0.85 (m, 6H) LC-MS: m/z=318 (MH)+.

後処理

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for about 5 hours
  3. customthe crude residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether (1:4))

出典と根拠

ORDレコード
ord-78995b4d748446c0aab3b3f8242e9a83
出典データセット
uspto-grants-2013_09
特許番号
US08524733B2

関連ノート

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