Hydrochloric Acid → 7-Methoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 1932303Notes

Reaction equation

HRID 1932303 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][N:11]=[C:12]2[CH3:15])=[CH:7][CH:6]=1.Cl>CO>[CH3:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][NH:11][CH:12]2[CH3:15])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 150619777-Methoxy-1-methyl-3,4-dihydroisoquinoline

Product 1

HCID 159400117-Methoxy-1-methyl-1,2,3,4-tetrahydroisoquinolineYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (3.81 g, 100.8 mmol) was slowly added at 0° C. to a solution of 7-methoxy-1-methyl-3,4-dihydroisoquinoline (14.72 g, 84 mmol) prepared in Step 2 in anhydrous methanol (100 ml). The reaction mixture was stirred overnight at room temperature. 1N hydrochloric acid was added to the reaction mixture, which was concentrated under reduced pressure, basified with potassium hydroxide, and then extracted with dichloromethane. The organic layer was washed with a saturated sodium chloride solution, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 11.01 g of the titled compound as brown oil. (Yield: 74%) The product was used in the subsequent step without further purification.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with a saturated sodium chloride solution
  4. dry with materialdried on anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a694d64ab4b349e38e7ddf045291e131
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

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