Potassium Hydroxide → 1-(5-(4-Fluorophenyl)-5-(3-pyridinyl)pentyl]-3-methylpiperazine

HRID 1494633Notes

Reaction equation

HRID 1494633 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16](C(OCC)=O)[CH:15]([CH3:24])[CH2:14]2)=[CH:4][CH:3]=1.[OH-].[K+]>CC(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][NH:16][CH:15]([CH3:24])[CH2:14]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 15167760Ethyl 4-[5-(4-fluorophenyl)-5-(3-pyridinyl)pentyl]2-methyl-1-piperazinecarboxylate

Product 1

HCID 150877501-(5-(4-Fluorophenyl)-5-(3-pyridinyl)pentyl]-3-methylpiperazineYield 67.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 12 parts of ethyl 4-[5-(4-fluorophenyl)-5-(3-pyridinyl)pentyl]-2-methyl-1-piperazinecarboxylate, 16 parts of potassium hydroxide and 128 parts of 2-propanol was stirred for 4 days at reflux temperature. After cooling, the reaction mixture was evaporated. Water was added to the residue and the mixture was evaporated till all traces of 2-propanol were removed (this was repeated twice). The residue was taken up in water and the product was extracted with dichlormethane. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichlormethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 6.7 parts (67.6%) of 1-[5-(4-fluorophenyl)-5-(3-pyridinyl)pentyl]-3-methylpiperazine as a residue (int. 39).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated
  4. additionWater was added to the residue
  5. customthe mixture was evaporated till all traces of 2-propanol
  6. customwere removed (
  7. extractionthe product was extracted with dichlormethane
  8. washThe extract was washed with water
  9. customdried
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was purified by column chromatography over silica gel using
  13. additiona mixture of trichlormethane and methanol
  14. customThe pure fractions were collected
  15. customthe eluent was evaporated

Sources & evidence

ORD record
ord-d3218eb0aa6d473e9301923c3b7961cc
Source dataset
uspto-grants-1991_06
Patent number
US05026853

Reaction notes

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