Hydrochloric Acid → 6-Methoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 275896Notes

Reaction equation

HRID 275896 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH3:13])=[N:8][CH2:7][CH2:6]2.[BH4-].[Na+].Cl.[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH3:13])[NH:8][CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 138591866-Methoxy-1-methyl-3,4-dihydroisoquinoline

Product 1

HCID 142302816-Methoxy-1-methyl-1,2,3,4-tetrahydroisoquinolineYield 82,627.602%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-methoxy-1-methyl-3,4-dihydroisoquinoline (54.0 g, 0.31 mmol) was added to a suspension of sodium borohydride(5.8 g, 138 mmol) in ethanol. The mixture solution was stirred for 1 hour at a room temperature, cooled to below 5° C., acidified with diluted hydrochloric acid, adjusted to alkali with sodium hydroxide solution, and then extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under a reduced pressure to give 45.4 g of the titled compound.

Workup

  1. temperaturecooled to below 5° C.
  2. extractionextracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-0d7c703eacdf49228d4185d8be026748
Source dataset
uspto-grants-2002_03
Patent number
US06352993B1

Reaction notes

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