Dimethylformamide → 3-[1-(4-methylphenylsulfonyl)piperidin-4-yl]-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one

HRID 1277260Notes

Reaction equation

HRID 1277260 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][C:27](O)=[O:28])=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.CN(C=O)C>C1COCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:12][CH2:13][CH:14]([C:17]3[CH:18]=[CH:19][C:20]4[CH2:23][CH2:24][CH2:25][CH2:26][C:27](=[O:28])[C:21]=4[CH:22]=3)[CH2:15][CH2:16]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 184723885-[4-[1-(4-Methylphenylsulfonyl)piperidin-4-yl]phenyl]pentanoic acid

Product 1

HCID 184724613-[1-(4-methylphenylsulfonyl)piperidin-4-yl]-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-oneYield 66.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-[4-[1-(4-methylphenylsulfonyl)-piperidin-4-yl]phenyl]pentanoic acid (0.50 g) in THF (10 ml) were added at room temperature oxalyl chloride (0.21 ml) and a drop of DMF, and the mixture was stirred for 1 hour. Under reduced pressure, the mixture was concentrated, and the residue was dissolved in dichloromethane (10 ml). To the mixture was added at 0° C. aluminum chloride (0.35 g), and the mixture was stirred at 0° C. for 30 minutes and then at room temperature for 5 minutes. The mixture was added to ice/water, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, saturated sodium bicarbonate solution and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the mixture was concentrated, and the residue was purified with column chromatography (ethyl acetate/hexane=1:2) to give colorless crystals of 3-[1-(4-methylphenylsulfonyl)-piperidin-4-yl]-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (0.32 g).

Workup

  1. concentrationUnder reduced pressure, the mixture was concentrated
  2. dissolutionthe residue was dissolved in dichloromethane (10 ml)
  3. additionTo the mixture was added at 0° C. aluminum chloride (0.35 g)
  4. waitat room temperature for 5 minutes
  5. additionThe mixture was added to ice/water
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with 1N hydrochloric acid, saturated sodium bicarbonate solution and saturated brine
  8. dry with materialdried with magnesium sulfate
  9. concentrationUnder reduced pressure, the mixture was concentrated
  10. customthe residue was purified with column chromatography (ethyl acetate/hexane=1:2)

Sources & evidence

ORD record
ord-82e2a80881e44877bc4d35b8a7c78add
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

Loading…