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Potassium Iodide → 1-(4-methoxyphenyl)-4-[4-(1H-pyrazol-1-yl)phenyl]piperazine

HRID 1154744
Notes
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Reaction equation

HRID 1154744 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:13][CH2:14]Cl)[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.[N:16]1([C:21]2[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=2)[CH:20]=[CH:19][CH:18]=[N:17]1.[I-].[K+].C(=O)([O-])O.[Na+]>O.CC(=O)C>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([N:4]2[CH2:13][CH2:14][N:27]([C:24]3[CH:23]=[CH:22][C:21]([N:16]4[CH:20]=[CH:19][CH:18]=[N:17]4)=[CH:26][CH:25]=3)[CH2:2][CH2:3]2)=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 15064N,N-Bis(2-chloroethyl)-4-methoxybenzenamineHCID 516892Sodium BicarbonateHCID 5942744-(1H-Pyrazol-1-yl)aniline

Product 1

HCID 128770311-(4-methoxyphenyl)-4-[4-(1H-pyrazol-1-yl)phenyl]piperazine

Reagents, catalysts & solvents 2

HCID 180
Acetone
Solvent
HCID 962WaterSolvent

Procedure

A mixture of 12.5 parts of N,N-bis(2-chloroethyl)-4-methoxybenzenamine, 8 parts of 4-(1H-pyrazol-1-yl)benzenamine, 2 parts of potassium iodide, 80 parts of 2-propanone and 100 parts of water is stirred and refluxed for 24 hours. The reaction mixture is cooled. The precipitated product is filtered off (the filtrate is set aside), washed with water and with 2-propanone, yielding a first crude fraction of 6 parts. The filtrate (see above) is neutralized with a sodium hydrogen carbonate solution and extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is triturated in 2-propanol. The product is filtered off and washed with methanol, yielding a second crude fraction of 2 parts. The combined crude crops (resp. 6 and 2 parts) are crystallized from 1-butanol, yielding 7.1 parts of 1-(4-methoxyphenyl)-4-[4-(1H-pyrazol-1-yl)phenyl]piperazine; mp. 207.7° C.

Workup

  1. temperaturerefluxed for 24 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationThe precipitated product is filtered off (the filtrate
  4. washwashed with water and with 2-propanone
  5. customyielding a first crude fraction of 6 parts
  6. extractionextracted with trichloromethane
  7. customThe extract is dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is triturated in 2-propanol
  11. filtrationThe product is filtered off
  12. washwashed with methanol
  13. customyielding a second crude fraction of 2 parts
  14. customare crystallized from 1-butanol

Sources & evidence

ORD record
ord-3340eb3f0e4b44db82a29c20fbb0bf40
Source dataset
uspto-grants-1984_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04490530

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes