2,6-Lutidine → 11-(3-fluorophenyl)-9-methoxy-3,4-dihydro-2H-pyrido[1,2-b]isoquinoline-1,6-dione

HRID 2196376Notes

Reaction equation

HRID 2196376 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[C:5]([C:7]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:8]=1[C:9](Cl)=[O:10])=O.Cl.[NH:22]1[CH2:27][CH2:26][CH2:25][C:24](=[O:28])[CH2:23]1.N1C(C)=CC=CC=1C>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:5]2[C:7]3[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:8]=3[C:9](=[O:10])[N:22]3[CH2:27][CH2:26][CH2:25][C:24](=[O:28])[C:23]=23)[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 22707028Piperidin-3-one hydrochlorideHCID 86040875HCID 86040875, compound

Product 1

HCID 1137112611-(3-fluorophenyl)-9-methoxy-3,4-dihydro-2H-pyrido[1,2-b]isoquinoline-1,6-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 2-(3-fluorobenzoyl)-4-methoxybenzoyl chloride (3.36 g) and piperidin-3-one hydrochloride (1.88 g) in 54 ml of toluene was added 2,6-lutidine (4.01 ml). The reaction was heated at reflux (3:10 pm) for 24 h, then partitioned between EtOAc and 400 mL of 1 N HCl. The aqueous solution was extracted twice more with EtOAc. The combined organic solutions were dried (MgSO4) and concentrated. Flash chromatography (40-100% EtOAc/hexanes) to gave the titled compound.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux (3:10 pm) for 24 h
  3. custompartitioned between EtOAc and 400 mL of 1 N HCl
  4. extractionThe aqueous solution was extracted twice more with EtOAc
  5. dry with materialThe combined organic solutions were dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9699b865e0244626bad8b3ea02051ec0
Source dataset
uspto-grants-2012_12
Patent number
US08338449B2

Reaction notes

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