Potassium Carbonate → HCID 9840034, compound

HRID 2414442Notes

Reaction equation

HRID 2414442 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][C:4](=[O:7])[NH:3]1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23]Cl)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[F:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][CH2:23][N:3]3[C:4](=[O:7])[CH2:5][CH2:6][C:2]3=[O:1])[CH2:19][CH2:20]2)=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11439SuccinimideHCID 106825561-(3-Chloropropyl)-4-(4-fluorophenyl)piperazine

Product 1

HCID 9840034HCID 9840034, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

Scheme-I: A mixture of 2,5-dioxopyrrolidine (0.500 g, 5 miol), 1-[4-(4-fluorophenyl) -piperazine-1-yl ]-3-chloropropane (1.28 g, 5 mmol), potassium carbonate (0.502 g, 3.75 mmol) and tetrabutylammonium bromide (0.322 g, 1mmol) in acetone (25 ml) was refluxed for 16 hours at 80° C. with stirring. The solvent was evaporated off in vacuo and the residue was suspended in water (80 ml). The aqueous solution was extracted with chloroform (3×50 ml), and the organic layers combined, washed with water (2×50 mnl), dried over Na2SO4 and evaporated in vacuo to give the title compound. The product was purified by column chromatography over flash silica gel using chloroform-methanol (98:2) as eluent; yield 1.00 g (65%), oil.

Workup

  1. customThe solvent was evaporated off in vacuo
  2. extractionThe aqueous solution was extracted with chloroform (3×50 ml)
  3. washwashed with water (2×50 mnl)
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-1bf0b1606acb4bc1982815d22cd538a4
Source dataset
uspto-grants-2004_11
Patent number
US06812344B1

Reaction notes

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