Hydrogen Bromide → 3-[4-(2-propenyl)-1-piperazinyl)-1-(4-fluorophenyl)-1H-indazole hydrobromide

HRID 655022Notes

Reaction equation

HRID 655022 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[N:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:29]([Br:32])[CH:30]=[CH2:31].Br>C(OCC)(=O)C.O.CN(C)C=O>[BrH:32].[CH2:31]([N:20]1[CH2:19][CH2:18][N:17]([C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[N:9]=2)[CH2:22][CH2:21]1)[CH:30]=[CH2:29]

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 151170821-(4-fluorophenyl)-3-(1-piperazinyl)-1H-indazole

Product 1

HCID 198870793-[4-(2-propenyl)-1-piperazinyl)-1-(4-fluorophenyl)-1H-indazole hydrobromideYield 33%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 5.0 g of 1-(4-fluorophenyl)-3-(1-piperazinyl)-1H-indazole, 2.6 g of potassium carbonate, 2.2 g of allyl bromide, and 75 ml of dimethylformamide was stirred at 70°-75° for 16 hours, and then at ambient temperature for 48 hours. The mixture was poured into water and the aqueous mixture was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated to produce an oil. The oil was dissolved in ethyl acetate and a saturated solution of hydrogen bromide in ethyl acetate was added, dropwise, until the solution was acidic. A precipitate was formed and collected. Recrystallization of the precipitate from ethanol gave 2.3 g (33%) of 3-[4-(2-propenyl)-1-piperazinyl)-1-(4-fluorophenyl)-1H-indazole hydrobromide.

Workup

  1. waitat ambient temperature for 48 hours
  2. extractionthe aqueous mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto produce an oil
  7. customA precipitate was formed
  8. customcollected
  9. customRecrystallization of the precipitate from ethanol

Sources & evidence

ORD record
ord-d59ea7eb8a8f46e684df7607f30ad587
Source dataset
uspto-grants-1992_07
Patent number
US05134236

Reaction notes

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