Sodium Hydroxide → 4-[1-(4-methylphenylsulfonyl)piperidin-4-yl]-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid

HRID 1388018Notes

Reaction equation

HRID 1388018 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[C:27]4[CH2:26][CH2:25][CH2:24][C:23]([C:28]([O:30]C)=[O:29])=[CH:22][C:21]=4[CH:20]=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH2:12][CH2:13][CH:14]([C:17]3[C:27]4[CH2:26][CH2:25][CH2:24][C:23]([C:28]([OH:30])=[O:29])=[CH:22][C:21]=4[CH:20]=[CH:19][CH:18]=3)[CH2:15][CH2:16]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18472663methyl 4-[1-(4-methylphenylsulfonyl)piperidin-4-yl]-6,7-dihydro-5H-benzocycloheptene-8-carboxylate

Product 1

HCID 184723754-[1-(4-methylphenylsulfonyl)piperidin-4-yl]-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acidYield 58.4%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of methyl 4-[1-(4-methylphenylsulfonyl)piperidin-4-yl]-6,7-dihydro-5H-benzocyclo-heptene-8-carboxylate (1.0 g) in ethanol/THF (20/40 ml) was added at room temperature 1N sodium hydroxide solution (2.7 ml), and the mixture was stirred for 13 hours. Under reduced pressure, the mixture was concentrated. To the mixture was added water, and the mixture was washed with ethyl acetate. To the aqueous layer was added 1N hydrochloric acid (5 ml), and the mixture was extracted with ethyl acetate/THF. The organic layer was washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the mixture was concentrated, and the resulting colorless crystals were collected by filtration, which were washed with hexane to give colorless crystals of 4-[1-(4-methylphenylsulfonyl)piperidin-4-yl]-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid (565.4 mg).

Workup

  1. concentrationUnder reduced pressure, the mixture was concentrated
  2. additionTo the mixture was added water
  3. washthe mixture was washed with ethyl acetate
  4. additionTo the aqueous layer was added 1N hydrochloric acid (5 ml)
  5. extractionthe mixture was extracted with ethyl acetate/THF
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried with magnesium sulfate
  8. concentrationUnder reduced pressure, the mixture was concentrated
  9. filtrationthe resulting colorless crystals were collected by filtration, which
  10. washwere washed with hexane

Sources & evidence

ORD record
ord-1a530bd16da34daebcea7099702572c7
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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