Sodium borohydride → HCID 59396390, compound

HRID 2383024Notes

Reaction equation

HRID 2383024 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([O:15][CH3:16])[CH:14]=1)[C:11]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[N:10][CH2:9][CH2:8]2>CCO>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([O:15][CH3:16])[CH:14]=1)[CH:11]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[NH:10][CH2:9][CH2:8]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67536456HCID 67536456, compound

Product 1

HCID 59396390HCID 59396390, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (450 mg) was added with stirring to a solution of 6,8-dimethoxy-1-phenyl-3,4-dihydroisoquinoline (1.96 g) in EtOH (50 mL) over 5 minutes. The reaction mixture was stirred at room temperature for 2 hours and then further stirred at 60° C. for 1.5 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. An aqueous 3 M HCl solution (60 mL) was added to the resulting residue, followed by heating under reflux for 3 minutes. After cooling, an aqueous 20% NaOH solution was added to the mixture to have strong alkalinity, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to obtain 6,8-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline (1.88 g).

Workup

  1. stirringfurther stirred at 60° C. for 1.5 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionAn aqueous 3 M HCl solution (60 mL) was added to the resulting residue
  5. temperatureby heating
  6. temperatureunder reflux for 3 minutes
  7. temperatureAfter cooling
  8. additionan aqueous 20% NaOH solution was added to the mixture
  9. extractionfollowed by extraction with chloroform
  10. washThe organic layer was washed with saturated brine
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2c12993d7922486cbef2342e86334e4e
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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