Sodium Carbonate → 1-[4-[4-[6-(Trifluoromethyl)-2-pyridinyl]-1-piperazinyl]-butyl]-2-pyrrolidinone

HRID 1646484Notes

Reaction equation

HRID 1646484 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[N:19]=[C:18]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC>[F:27][C:13]([F:12])([F:26])[C:14]1[N:19]=[C:18]([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:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 114247401-[6-(Trifluoromethyl)pyridin-2-yl]piperazineHCID 152878411-(4-Bromobutyl)pyrrolidin-2-one

Product 1

HCID 152878441-[4-[4-[6-(Trifluoromethyl)-2-pyridinyl]-1-piperazinyl]-butyl]-2-pyrrolidinoneYield 102.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

9 g of 1-(4-bromobutyl)-2-pyrrolidinone and 7.6 g of 1-[6-(trifluoromethyl)-2-pyridinyl]-piperazine were mixed with 100 ml of butanol. 4.3 g of sodium carbonate were added, and the mixture is refluxed for 3 hours. The precipitate is filtered and washed with butanol, and the filtrate is then evaporated. The residue was dissolved in dichloromethane, washed with water, dried over anhydrous magnesium sulfate, after which the solvent was evaporated to obtain 12.5 g of 1-[4-[4-[6-(trifluoromethyl)-2-pyridinyl]-1-piperazinyl]-butyl]-2-pyrrolidinone. To make the monofumarate, the free base was mixed with 3.9 g of fumaric acid in absolute ethanol. The resulting substance was recrystallized twice from absolute ethanol, after which 7.8 g (43.6% yield) of 1-[4-[4-[6-(trifluoromethyl)-2-pyridinyl]-1-piperazinyl]butyl]-2pyrrolidinone. (E)-2-butenedioate (1:1) salt were obtained. M.p. 173° C.

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. filtrationThe precipitate is filtered
  3. washwashed with butanol
  4. customthe filtrate is then evaporated
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customafter which the solvent was evaporated

Sources & evidence

ORD record
ord-ff4d1521199e4e23ada3dbfc3fd5e319
Source dataset
uspto-grants-1993_01
Patent number
US05180726

Reaction notes

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