Water → HCID 20566241, compound

HRID 2390025Notes

Reaction equation

HRID 2390025 reaction equation
[CH2:1]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>CO.[Ni](Cl)Cl>[CH2:1]([CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][NH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 27529323-benzylisoquinolineHCID 4311764Sodium borohydride

Product 1

HCID 20566241HCID 20566241, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Procedure

2.21 g of 3-benzylisoquinoline and 2.88 g of nickel dichloride.hexahydrate were dissolved in 50 mL of methanol at room temperature, and 4.58 g of sodium borohydride was added thereto over 30 minutes, followed by further stirring at room temperature for 4 hours. After completion of the reaction, water was added to the reaction liquid, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue obtained was purified using silica gel chromatography (chloroform:methanol=100:1→50:1) to obtain 1.85 g (yield 82%) of a title compound as a light yellow oily substance.

Workup

  1. additionwas added to the reaction liquid
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified

Sources & evidence

ORD record
ord-38cfe2a2096f4a9bad8df58c897842a9
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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