Sodium Hydroxide → 3-(1-(3-(Thioxanthen-9-ylidene)-1-propyl)piperidin-4-yl)propionic acid acetate

HRID 1952829Notes

Reaction equation

HRID 1952829 reaction equation
[CH:1]1[C:14]2[C:13](=[CH:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][C:26]([O:28]CC)=[O:27])[CH2:20][CH2:19]3)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(O)(=O)C([O-])=O.[OH-].[Na+]>C(O)C>[C:26]([OH:28])(=[O:27])[CH3:25].[CH:1]1[C:14]2[C:13](=[CH:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][CH:21]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH2:22][CH2:23]3)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 3716971Hydrogen oxalate monoanionHCID 23301314Ethyl 3-(1-(3-(thioxanthen-9-ylidene)-1-propyl)piperidin-4-yl)propionate

Product 1

HCID 702939563-(1-(3-(Thioxanthen-9-ylidene)-1-propyl)piperidin-4-yl)propionic acid acetateYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-(1-(3-(thioxanthen-9-ylidene)-1-propyl)piperidin-4-yl)propionate (as the free base released from the above hydrogen oxalate; 3.71 g, 0.0088 mol), 4 N sodium hydroxide (10 ml) and 96% ethanol (70 ml) was stirred at room temperature overnight. Ethanol was evaporated in vacuo, the residue was dissolved in water (50 ml) and the aqueous solution was washed with diethyl ether (50 ml). The aqueous phase was neutralised with acetic acid and extracted with dichloromethane (3×150 ml). The combined dichloromethane extracts tracts were dried (MgSO4) and evaporated in vacuo. The residue was dissolved in acetone (30 ml), the solution was diluted with diethyl ether (30 ml) and the mixture was stirred for 1 h. The precipitated solid was filtered off, washed with acetone and dried in vacuo, affording 2.24 g (56%) of the title compound.

Workup

  1. customEthanol was evaporated in vacuo
  2. dissolutionthe residue was dissolved in water (50 ml)
  3. washthe aqueous solution was washed with diethyl ether (50 ml)
  4. extractionextracted with dichloromethane (3×150 ml)
  5. dry with materialwere dried (MgSO4)
  6. customevaporated in vacuo
  7. dissolutionThe residue was dissolved in acetone (30 ml)
  8. additionthe solution was diluted with diethyl ether (30 ml)
  9. filtrationThe precipitated solid was filtered off
  10. washwashed with acetone
  11. customdried in vacuo

Sources & evidence

ORD record
ord-65bb4b7117894c50910dff040ea4b677
Source dataset
uspto-grants-2000_09
Patent number
US06114354

Reaction notes

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