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

HRID 68639Notes

Reaction equation

HRID 68639 reaction equation
[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]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 67164894HCID 67164894, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-313e6e3a2c3b4af79543d3bb44c013f8
Source dataset
uspto-grants-2014_09
Patent number
US08822459B2

Reaction notes

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