Water → 6,7-Dimethoxy-2-(piperidin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline

HRID 1393030Notes

Reaction equation

HRID 1393030 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[CH2:15][N:14]([C:21]([CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=O)[CH2:13][CH2:12]2.O.[OH-].[Na+]>O1CCCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[CH2:15][N:14]([CH2:21][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[CH2:13][CH2:12]2

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23133306HCID 23133306, compound

Product 1

HCID 231333026,7-Dimethoxy-2-(piperidin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1 M solution of LiAlH4 in dry tetrahydrofuran (12 ml) was added dropwise to a solution of (6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)(piperidin-4-yl)methanone (2 g, 6.6 mmol) in dry tetrahydrofuran (60 ml) under argon atmosphere. The mixture was refluxed overnight. Water was added to the crude, made alkaline with 1 N NaOH and the salts formed was filtered over celite. Extraction with ethyl acetate yielded a solution that was dried with Na2SO4 and concentrated in vacuo to give and oil that was purified by flash chromatography.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customthe salts formed
  3. filtrationwas filtered over celite
  4. extractionExtraction with ethyl acetate
  5. customyielded a solution that
  6. dry with materialwas dried with Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto give
  9. customoil that was purified by flash chromatography

Sources & evidence

ORD record
ord-5b8612223c60439db6fad2af60eb7619
Source dataset
uspto-grants-2008_03
Patent number
US07345057B2

Reaction notes

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