Water → HCID 19418914, compound

HRID 864355Notes

Reaction equation

HRID 864355 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[CH2:15][CH2:16][CH2:17][N:18]1[C:29]2=[C:30]3[C:25](=[CH:26][CH:27]=[CH:28]2)[CH:24]=[CH:23][CH:22]=[C:21]3[NH:20][C:19]1=[O:31].C(=O)(O)[O-].[Na+].O>CN(C)C=O.ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:15][CH2:16][CH2:17][N:18]3[C:29]4=[C:30]5[C:25](=[CH:26][CH:27]=[CH:28]4)[CH:24]=[CH:23][CH:22]=[C:21]5[NH:20][C:19]3=[O:31])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 752601-(4-Fluorophenyl)piperazineHCID 516892Sodium BicarbonateHCID 19418925HCID 19418925, compound

Product 1

HCID 19418914HCID 19418914, compoundYield 22.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

1.35 g of 4-(4-fluorophenyl)piperazine, 1.84 g of 1-(3-chloropropyl)-2-perimidinone and 0.66 g of sodium bicarbonate, in 25 cm3 of dry N,N-dimethylformamide are stirred at the reflux temperature of the solvent for 2 hours. The reaction mixture is cooled and poured into a mixture of 20 cm3 of water and 25 cm3 of dichloro-methane. The organic phase is decanted, washed with water (3×15 cm3), dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column under a pressure of 0.7 bar of nitrogen, eluting with ethyl acetate. 0.65 g of 1-{3-[4-(4-fluorophenyl)-1-piperazinyl]-propyl }-2-perimidinone is thus obtained; melting point =206° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customThe organic phase is decanted
  3. washwashed with water (3×15 cm3)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe residue is chromatographed on a silica gel column under a pressure of 0.7 bar of nitrogen
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-c1630324bbaf48c4b9f8e9956df4ae53
Source dataset
uspto-grants-1996_10
Patent number
US05563144

Reaction notes

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