Water → 6-Methoxy-2-(methylethyl)-1-{4-[(2-piperidyl)ethoxy]benzyl}-1,2,3,4-tetrahydroisoquinoline

HRID 1180149ノート

反応式

HRID 1180149 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17](O)=[CH:16][CH:15]=1)[N:8]([CH:21]([CH3:23])[CH3:22])[CH2:7][CH2:6]2.Cl.ClCC[N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[C:34](=[O:37])([O-])[O-].[K+].[K+].O.[CH3:41]N(C)C=O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:37][CH2:34][CH2:41][CH:33]3[CH2:32][CH2:31][CH2:30][CH2:29][NH:28]3)=[CH:18][CH:19]=1)[N:8]([CH:21]([CH3:22])[CH3:23])[CH2:7][CH2:6]2

参加物

6

反応物 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 234407376-Methoxy-2-(methylethyl)-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline

生成物 1

HCID 536880276-Methoxy-2-(methylethyl)-1-{4-[(2-piperidyl)ethoxy]benzyl}-1,2,3,4-tetrahydroisoquinoline収率 70%

反応条件

温度
80 °C

実験手順

A mixture of 6-methoxy-2-(methylethyl)-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline (0.212 g, 0.68 mmol), 2-chloroethylpiperidine hydrochloride (0.25 g, 1.36 mmol), and potassium carbonate (0.47 g, 3.4 mmol) in dimethylformamide (10 mL) was heated at 80° C. overnight. After cooling to room temperature, the mixture was poured into water and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was then purified by chromatography (SiO2, 0-15% methanol/CH2Cl2) to provide the title compound (0.201 g, 70% yield): ES-MS (m/z) 423 [M+H]+.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was then purified by chromatography (SiO2, 0-15% methanol/CH2Cl2)

出典と根拠

ORDレコード
ord-075f759e14444b629c7dacc24aa0da3b
出典データセット
uspto-grants-2007_10
特許番号
US07279489B2

反応ノート

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