(4-Bromobutoxy)benzene → 1-(4-phenoxybutyl)piperazine

HRID 638534Notes

Reaction equation

HRID 638534 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][CH2:11]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)=O>CC(O)C>[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70986(4-Bromobutoxy)benzeneHCID 821911-Piperazinecarboxaldehyde

Product 1

HCID 4095541-(4-phenoxybutyl)piperazineYield 71.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 45.8 g (0.2 moles) of 4-phenoxybutyl bromide and 45.6 g (0.4 moles) of 1-formylpiperazine in 500 ml of 2-propanol was heated at reflux for 18 hours. The mixture was cooled and filtered. The filter was washed with 2-propanol and the filtrate was evaporated to a paste in vacuo. Water was added and the mixture was extracted three times with 200 ml portions of chloroform. The extracts were combined and evaporated to dryness. Then 250 ml of 5N sodium hydroxide was added to the residue. The mixture was refluxed for 18 hours with stirring, cooled and extracted twice with 250 ml portions of chloroform. The extracts were combined, dried over magnisium sulfate and evaporated to an oil. The oil was distilled bp 153°-156° C./0.05 mm of mercury and gave 33.4 g of 1-(4-phenoxybutyl)piperazine as a colorless liquid which crystallized on standing, mp 35°-36° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. washThe filter was washed with 2-propanol
  6. customthe filtrate was evaporated to a paste in vacuo
  7. additionWater was added
  8. extractionthe mixture was extracted three times with 200 ml portions of chloroform
  9. customevaporated to dryness
  10. additionThen 250 ml of 5N sodium hydroxide was added to the residue
  11. temperatureThe mixture was refluxed for 18 hours
  12. temperaturecooled
  13. extractionextracted twice with 250 ml portions of chloroform
  14. dry with materialdried over magnisium sulfate
  15. customevaporated to an oil
  16. distillationThe oil was distilled bp 153°-156° C./0.05 mm of mercury

Sources & evidence

ORD record
ord-4ce0b95cef2b4c6c91849d74186490fc
Source dataset
uspto-grants-1985_12
Patent number
US04562189

Reaction notes

Loading…