Water → Methyl 2-benzyl-6-fluoro-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

HRID 2390037Notes

Reaction equation

HRID 2390037 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][NH:7][CH:6]([C:12]([O:14][CH3:15])=[O:13])[CH2:5]2.[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH2:16]([N:7]1[CH:6]([C:12]([O:14][CH3:15])=[O:13])[CH2:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[CH2:8]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 57947410Methyl 6-fluoro-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Product 1

HCID 59323112Methyl 2-benzyl-6-fluoro-1,2,3,4-tetrahydroisoquinoline-3-carboxylateYield 46%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

702 mg of methyl 6-fluoro-1,2,3,4-tetrahydroisoquinoline-3-carboxylate, 425 mg of benzyl chloride, and 425 mg of potassium carbonate were dissolved in 5 mL of acetonitrile, followed by stirring under reflux for 3 hours. Water was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was then washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was purified using silica gel chromatography (acetone:n-hexane=1:20) to obtain 460 mg (yield 46%) of a title compound as a pale yellow oily substance.

Workup

  1. temperatureunder reflux for 3 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was then 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-9414bcf1ffcb4e679b05a85f28d51a24
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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