Hydrochloric Acid → 1-Methyl-1,2,3,4-tetrahydroisoquinoline

HRID 1264891Notes

Reaction equation

HRID 1264891 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][N:5]=1.Cl.[OH-].[Na+]>C(O)C>[CH3:3][CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][NH:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2315021-Methyl-3,4-dihydroisoquinolineHCID 4311764Sodium borohydride

Product 1

HCID 922141-Methyl-1,2,3,4-tetrahydroisoquinolineYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the suspension of sodium borohydride (5.28 g, 138 mmol) in ethanol, was added the compound (19.8 g, 133.8 mmol) prepared in Step 2 above. The reaction mixture was stirred for 1 hour at room temperature, cooled to below 5° C. acidified with diluted hydrochloric acid, neutralized with sodium hydroxide solution, and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give 18.5 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 in vacuo

Sources & evidence

ORD record
ord-0fa1402e6a6f4ab190954b032f6929b3
Source dataset
uspto-grants-2003_04
Patent number
US06545008B1

Reaction notes

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