Sodium Iodide → HCID 14986606, compound

HRID 373871Notes

Reaction equation

HRID 373871 reaction equation
[C:1]1([CH:7]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[CH:29]=[C:28]([C:30]([O:32]CC)=[O:31])[CH:27]=[N:26]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(C(C)=O)C>[C:1]1([CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:14]2[CH2:15][CH2:16][N:17]([CH2:21][CH2:22][CH2:23][CH2:24][N:25]3[CH:29]=[C:28]([C:30]([OH:32])=[O:31])[CH:27]=[N:26]3)[CH2:18][CH2:19]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 70048BenzhydrylpiperazineHCID 14986591HCID 14986591, compound

Product 1

HCID 14986606HCID 14986606, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Under reflux for 4 hours is placed a mixture of 6.3 g (25 mmoles) of diphenylmethyl piperazine, 6.87 g (25 mmoles) of 1-(4-bromobutyl)-4-ethyloxycarbonylpyrazole, 5.17 g (37.5 moles) of potassium carbonate and 5.06 g (33.7 mmoles) of sodium iodide in 100 ml of methyl ethyl ketone. It is cooled, filtered and the filtrate evaporated to dryness. The residue is taken up again with chloroform and water, the organic phase is dried with Na2SO4, it is filtered and evaporated under vacuum. The resulting product is purified on a chromatographic silica column (eluant: chloroform-methanol 95:5) and in this way 7.4 g of 1-[4-(4-Diphenylmethyl-1-piperazinyl)butyl]-4-ethyloxycarbonylpyrazole is obtained, with a melting point 70°-74° C.

Workup

  1. temperatureUnder reflux for 4 hours
  2. temperatureIt is cooled
  3. filtrationfiltered
  4. customthe filtrate evaporated to dryness
  5. dry with materialthe organic phase is dried with Na2SO4, it
  6. filtrationis filtered
  7. customevaporated under vacuum
  8. customThe resulting product is purified on a chromatographic silica column (eluant: chloroform-methanol 95:5) and in this way 7.4 g of 1-[4-(4-Diphenylmethyl-1-piperazinyl)butyl]-4-ethyloxycarbonylpyrazole
  9. customis obtained, with a melting point 70°-74° C.

Sources & evidence

ORD record
ord-46c75c5b820a4dad9b3a1c37754b7441
Source dataset
uspto-grants-1992_11
Patent number
US05166205

Reaction notes

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