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

HRID 2293124Notes

Reaction equation

HRID 2293124 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

1.76g of sodium borohydride(46 mM) was suspended in 80 ml of ethanol, and 6.48 g of the compound(44.6 mM) prepared in Step 2 above was added thereto. The resultant mixture was stirred at an ambient temperature for an hour and cooled to below 5° C., which was then acidified by adding dilute hydrochloric acid. After making the reaction solution alkaline by adding sodium hydroxide, it was extracted from ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under a reduced pressure to give 6.17 g of the title compound as oily substance.

Workup

  1. temperaturecooled to below 5° C.
  2. extractionwas extracted from 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-d6463ff2312e4f36880f643bfc274709
Source dataset
uspto-grants-1997_11
Patent number
US05686458

Reaction notes

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