Sodium Carbonate → ORG-13011 fumarate

HRID 1646483Notes

Reaction equation

HRID 1646483 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11].[F:12][C:13]([F:27])([F:26])[C:14]1[CH:19]=[CH:18][N:17]=[C:16]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38]>C(O)CCC.C(O)C>[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38].[F:26][C:13]([F:12])([F:27])[C:14]1[CH:19]=[CH:18][N:17]=[C:16]([N:20]2[CH2:21][CH2:22][N:23]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[CH2:10][CH2:9][CH2:8][C:7]3=[O:11])[CH2:24][CH2:25]2)[CH:15]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 444972Fumaric AcidHCID 112184921-[4-(Trifluoromethyl)pyridin-2-yl]piperazineHCID 152878411-(4-Bromobutyl)pyrrolidin-2-one

Product 1

HCID 70682615ORG-13011 fumarateYield 52%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 702EthanolSolvent

Procedure

2 7 g of 1-(4-bromobutyl)-2-pyrrolidinone were mixed with 2.2 g of 1-[4-(trifluoromethyl)-2-pyridinyl]piperazine dissolved in 30 ml of butanol, after which 1.3 g of sodium carbonate were added. The mixture was refluxed for 2 hours, after which the precipitate was filtered and washed with butanol. The solvent was evaporated and the residue was dissolved in dichloromethane, washed with water, and dried over anhydrous magnesium sulfate. After evaporation of the solvent 3.4 g of 1-[4-[4-[4-(trifluoromethyl)-2-pyridinyl]-1-piperazinyl]butyl]-2-pyrrolidinone were obtained. To make the monofumarate, 1 g of fumaric acid dissolved in absolute ethanol was mixed with the free base. The resulting compound was recrystallized twice from acetonitrile, after which 2.4 g (52% yield) of 1-[4-[4-[4-(trifluoromethyl)-2-pyridinyl]-1-piperazinyl]butyl]-2pyrrolidinone (E)-2-butenedioate (1:1) salt were obtained with a melting point of 140° C.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. filtrationafter which the precipitate was filtered
  3. washwashed with butanol
  4. customThe solvent was evaporated
  5. dissolutionthe residue was dissolved in dichloromethane
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter evaporation of the solvent 3.4 g of 1-[4-[4-[4-(trifluoromethyl)-2-pyridinyl]-1-piperazinyl]butyl]-2-pyrrolidinone
  9. customwere obtained
  10. additionwas mixed with the free base
  11. customThe resulting compound was recrystallized twice from acetonitrile

Sources & evidence

ORD record
ord-8b56b05798a44d2e966ff6125932fd2b
Source dataset
uspto-grants-1993_01
Patent number
US05180726

Reaction notes

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