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

HRID 68639노트

반응식

HRID 68639 반응식
[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]

참가 물질

5

반응물 3

HCID 962WaterHCID 8471TriethylamineHCID 67164894HCID 67164894, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-313e6e3a2c3b4af79543d3bb44c013f8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822459B2

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