Water → 2-[4-(Dipropylamino)butyl]-1,2,3,4-tetrahydro-6-isoquinolinecarboaldehyde

HRID 68639ノート

反応式

HRID 68639 の反応式
[CH2:1]([N:4]([CH2:21][CH2:22][CH3:23])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][OH:20])[CH:15]=2)[CH2:10]1)[CH2:2][CH3:3].C(N(CC)CC)C.O>CS(C)=O>[CH2:21]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:19]=[O:20])[CH:15]=2)[CH2:10]1)[CH2:22][CH3:23]

参加物

5

反応物 3

HCID 962WaterHCID 8471TriethylamineHCID 67164894HCID 67164894、化合物

生成物 1

HCID 866542922-[4-(Dipropylamino)butyl]-1,2,3,4-tetrahydro-6-isoquinolinecarboaldehyde収率 99.8%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution of the compound 21 (2.28 g) and triethylamine (4.99 mL) in dimethyl sulfoxide (30 mL), a sulfur trioxide-pyridine complex (2.28 g) was slowly added. The reaction mixture was stirred at room temperature for one hour. To the reaction solution, water (100 mL) was added. The aqueous layer was extracted twice with dichloromethane (50 mL). The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel chromatography (ethyl acetate:methanol:triethylamine=10:1:0→10:1:0.5) to obtain the title compound (2.26 g) having the following physical properties.

後処理

  1. extractionThe aqueous layer was extracted twice with dichloromethane (50 mL)
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (ethyl acetate:methanol:triethylamine=10:1:0→10:1:0.5)

出典と根拠

ORDレコード
ord-313e6e3a2c3b4af79543d3bb44c013f8
出典データセット
uspto-grants-2014_09
特許番号
US08822459B2

反応ノート

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