1-Bromo-3-chloropropane → HCID 19068116, compound

HRID 1957521Notes

Reaction equation

HRID 1957521 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.Cl[CH2:20][CH2:21][CH2:22]Br.[C:24]1(=[O:34])[NH:28][C:27](=[O:29])[C:26]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:25]12.[K]>C(O)C.C(N(CC)CC)C>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:20][CH2:21][CH2:22][N:28]2[C:24](=[O:34])[C:25]3[C:26](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:27]2=[O:29])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 80061-Bromo-3-chloropropaneHCID 8028TetrahydrofuranHCID 759941-BenzylpiperazineHCID 24194345Phthalimide potassium salt

Product 1

HCID 19068116HCID 19068116, compoundYield 102.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

44 g benzylpiperazine, 200 ml absolute THF, 39.4 g 1-chloro-3-bromopropane and 76 g triethylamine are heated for 8 hours under reflux. After separating the precipitate the tetrahydrofuran is concentrated by evaporation, the residue is dissolved in 500 ml ether, treated twice with carbon and subsequently the solvent is removed by distillation. After distillation in a high vacuum 1-benzyl-4-(3-chloropropyl)piperazine with a boiling point of 145°-148° C./0.3 mm Hg is obtained. 22.75 g of this distillate was dissolved in 200 ml ethanol and admixed with 15 g potassium phthalimide and it was heated for 56 hours under reflux. Subsequently the solvent was evaporated, the residue was dissolved in 150 ml dichloromethane and the organic phase was washed three times with 50 ml two molar sodium hydroxide solution and three times with 50 ml water. Afterwards the organic phase was dried and evaporated. 30 g 2-[3-(4-benzylpiperazin-1-yl)propyl]isoindol-1,3-dione is obtained as a viscous oil. TLC (mobile solvent: heptane/methyl ethyl ketone/ammonia atmosphere 2:1), Rf=0.32.

Workup

  1. temperatureunder reflux
  2. customAfter separating the precipitate the tetrahydrofuran
  3. concentrationis concentrated by evaporation
  4. dissolutionthe residue is dissolved in 500 ml ether
  5. additiontreated twice with carbon
  6. customsubsequently the solvent is removed by distillation
  7. distillationAfter distillation in a high vacuum 1-benzyl-4-(3-chloropropyl)piperazine with a boiling point of 145°-148° C./0.3 mm Hg
  8. customis obtained
  9. temperaturewas heated for 56 hours
  10. temperatureunder reflux
  11. customSubsequently the solvent was evaporated
  12. dissolutionthe residue was dissolved in 150 ml dichloromethane
  13. washthe organic phase was washed three times with 50 ml two molar sodium hydroxide solution and three times with 50 ml water
  14. customAfterwards the organic phase was dried
  15. customevaporated

Sources & evidence

ORD record
ord-281e708634a94d5cbd1678458e50c0b3
Source dataset
uspto-grants-1998_07
Patent number
US05786371

Reaction notes

Loading…