1-Benzylpiperazine → HCID 20568366, compound

HRID 1578275Notes

Reaction equation

HRID 1578275 reaction equation
[CH2:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:15])=[C:11](Cl)[CH:12]=2)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]1)[CH:2]=[CH2:3].[CH2:20]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CS(C)=O>[CH2:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:15])=[C:11]([N:30]3[CH2:31][CH2:32][N:27]([CH2:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:28][CH2:29]3)[CH:12]=2)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 759941-BenzylpiperazineHCID 12733883HCID 12733883, compound

Product 1

HCID 20568366HCID 20568366, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

2.8 g (0.01 mol) of 1-allyl-7-chloro-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, 7.2 g (0.04 mol) of 4-benzylpiperzine and 15 cm3 of DMSO were stirred and heated at 110° C. for 6 hours. The solvent was removed by distillation in vacuo. The residue was taken up in 40 cm3 of water. The suspension was adjusted to pH 7.3 by adding acetic acid. The precipitate was extracted with chloroform (4×20 cm3). The combined organic extracts were washed with water and then evaporated to dryness to give a viscous residue which crystallized on mixing with 10 cm3 of isopropanol. The solid was separated and recrystallised from methylcellosolve (30 cm3). 1.5 g of the acid, m.p. 209° C., were obtained.

Workup

  1. customThe solvent was removed by distillation in vacuo
  2. additionby adding acetic acid
  3. extractionThe precipitate was extracted with chloroform (4×20 cm3)
  4. washThe combined organic extracts were washed with water
  5. customevaporated to dryness
  6. customto give a viscous residue which
  7. customcrystallized
  8. additionon mixing with 10 cm3 of isopropanol
  9. customThe solid was separated
  10. customrecrystallised from methylcellosolve (30 cm3)

Sources & evidence

ORD record
ord-57d6c187484b48508e726e86e3128beb
Source dataset
uspto-grants-1981_09
Patent number
US04292317

Reaction notes

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