Potassium Carbonate → 6-benzylamino-3,4-dihydro-2H-isoquinolin-1-one

HRID 1947637

Reaction equation

HRID 1947637 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[NH:7][CH2:6][CH2:5]2.[C:13](=[O:16])([O-])[O-].[K+].[K+]>C(N)C1C=CC=CC=1>[CH2:8]([NH:7][C:6]1[CH:5]=[C:4]2[C:3](=[CH:2][CH:11]=1)[C:13](=[O:16])[NH:7][CH2:6][CH2:5]2)[C:9]1[CH:10]=[CH:11][CH:2]=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 107257096-Fluoro-1,2,3,4-tetrahydroisoquinolin-1-one

Product 1

HCID 672239156-benzylamino-3,4-dihydro-2H-isoquinolin-1-oneYield 35%

Reagents, catalysts & solvents 1

HCID 7504BenzylamineSolvent

Procedure

A solution of 6-fluoro-3,4-dihydro-2H-isoquinolin-1-one (300 mg, 1.81 mmol) and potassium carbonate (550 mg, 3.98 mmol) in benzylamine (1.5 ml) was stirred at 180° C. in a microwave for 2 hrs. The solvent was evaporated and the resulting residue partitioned between ethyl acetate (10 ml) and water (10 ml). The organic phase was separated, washed with brine (10 ml), then dried (MgSO4) and evaporated in vacuo. The crude residue was purified by preparative HPLC (Method A) to yield the title compound as a colourless solid (80 mg, 18%). HPLC retention time 3.81 min. Mass spectrum (ES+) m/z 253 (M+H).

Workup

  1. customThe solvent was evaporated
  2. customthe resulting residue partitioned between ethyl acetate (10 ml) and water (10 ml)
  3. customThe organic phase was separated
  4. washwashed with brine (10 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customThe crude residue was purified by preparative HPLC (Method A)

Sources & evidence

ORD record
ord-fa7e5e71fe5642d8a90aa87b2e5ae477
Source dataset
uspto-grants-2013_03
Patent number
US08399481B2

Linked notes

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