Water → 6-Methoxy-1,2,3,4-tetrahydroisoquinoline

HRID 352856Notes

Reaction equation

HRID 352856 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[N:8][CH2:7][CH2:6]2.O.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 1001219614446-29-8

Product 1

HCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (100 ml), 6-methoxy-3,4-dihydroisoquinoline (10.4 g) was dissolved. To the resulting solution, water (10 ml) and then sodium borohydride (6.10 g) were added. The resulting mixture was stirred at room temperature for 15 minutes. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane, followed by washing with water. The organic layer thus separated was dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (dichloromethane˜dichloromethane:methanol=100:15), whereby the title compound (7.95 g, 76%) was obtained.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washby washing with water
  4. customThe organic layer thus separated
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by chromatography on a silica gel column (dichloromethane˜dichloromethane:methanol=100:15), whereby the title compound (7.95 g, 76%)
  9. customwas obtained

Sources & evidence

ORD record
ord-96d7074cc17f49c7b1d6adb0ff5be15d
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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