Water → HCID 15117075, compound

HRID 359009Notes

Reaction equation

HRID 359009 reaction equation
[C:1]1([NH:7][N:8]=[C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2F)[N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].O>O1CCCC1>[C:1]1([N:7]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:9]([N:10]3[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 54170249HCID 54170249, compound

Product 1

HCID 15117075HCID 15117075, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution, under nitrogen of 12.4 g of 1-[(phenylhydrazono)(2-fluorophenyl)methyl]-4-methylpiperazine in 100 ml of a solution of tetrahydrofuran was added dropwise, 5.3 g of potassium t-butoxide in 50 ml of tetrahydrofuran. Following the addition, the reaction mixture was stirred at ambient temperature for 1 hour, poured into water, and extracted with dichloromethane. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated to an oil. The oil was purified on a Water's Model 500 Preparative High Pressure Liquid Chromatograph utilizing two silica gel columns and dichloromethane/methanol (4%) as the eluent. Concentration of the appropriate fractions gave 7.0 g (61%) of 1-phenyl-3-(4-methyl-1-piperazinyl)-1H indazole. Treatment of 3.1 g of the indazole with ethereal hydrogen chloride produced the hydrochloride salt. Recrystallization from ethanol gave 2.8 g of 1-phenyl-3-(4-methyl-1-piperazinyl)-1H-indazole hydrochloride, mp 244°-246°.

Workup

  1. additionthe addition
  2. extractionextracted with dichloromethane
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to an oil
  6. customThe oil was purified on a Water'

Sources & evidence

ORD record
ord-b71af364658746fb800bf59f4155de1f
Source dataset
uspto-grants-1991_03
Patent number
US04999356

Reaction notes

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