Ethanol → 4-(1-(3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propyl)piperidin-4-yl)-butyric acid hydrogen oxalate

HRID 1952831Notes

Reaction equation

HRID 1952831 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]=[C:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][CH2:20][C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]2=3)[CH2:10][CH2:9]1)C.[OH-:33].[Na+].C([OH:37])C>>[C:4]([OH:3])(=[O:32])[C:5]([OH:37])=[O:33].[CH:27]1[C:22]2[CH2:21][CH2:20][C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=3[C:17](=[CH:16][CH2:15][CH2:14][N:11]3[CH2:10][CH2:9][CH:8]([CH2:7][CH2:6][CH2:5][C:4]([OH:32])=[O:3])[CH2:13][CH2:12]3)[C:23]=2[CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 540820164-(1-(3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propyl)piperidin4-yl)butyric acid ethyl ester

Product 1

HCID 702958314-(1-(3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propyl)piperidin-4-yl)-butyric acid hydrogen oxalateYield 77%

Procedure

The above ester (6.7 g, 15.9 mmol) was dissolved in ethanol (30 ml) and 20% sodium hydroxide (10 ml) was added. After stirring for 3 days, ethanol was evaporated in vacuo, water (50 ml) and diethyl ether (50 ml) were added and the phases were separated. The water phase was treated with acetic acid and extracted with dichloromethane. The organic phase was dried (MgSO4) and the solvent was evaporated in vacuo. The residue (7.0 g) was dissolved in acetone (30 ml) and treated with a solution of oxalic acid dihydrate (2.0 g) in acetone (10 ml). The precipitate was filtered off and dried, affording 6.1 g (77%) of the title compound.

Workup

  1. customethanol was evaporated in vacuo, water (50 ml) and diethyl ether (50 ml)
  2. additionwere added
  3. customthe phases were separated
  4. additionThe water phase was treated with acetic acid
  5. extractionextracted with dichloromethane
  6. dry with materialThe organic phase was dried (MgSO4)
  7. customthe solvent was evaporated in vacuo
  8. dissolutionThe residue (7.0 g) was dissolved in acetone (30 ml)
  9. additiontreated with a solution of oxalic acid dihydrate (2.0 g) in acetone (10 ml)
  10. filtrationThe precipitate was filtered off
  11. customdried

Sources & evidence

ORD record
ord-762b4ebb475342ee8d11e1ddead502f0
Source dataset
uspto-grants-2000_09
Patent number
US06114354

Reaction notes

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