Potassium Hydroxide → 1-(4-fluorophenyl)-3-(1-piperazinyl)-1H-indazole

HRID 655021Notes

Reaction equation

HRID 655021 reaction equation
[OH-].[K+].C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[N:15]=2)[CH2:10][CH2:9]1)=O)C.COC(O)C>O>[F:29][C:26]1[CH:25]=[CH:24][C:23]([N:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[N:15]2)=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 30156371-MethoxyethanolHCID 151170814-[1-(4-fluorophenyl)-1H-indazol-3-yl]-1-piperazine carboxylic acid ethyl ester

Product 1

HCID 151170821-(4-fluorophenyl)-3-(1-piperazinyl)-1H-indazoleYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A stirred solution of 9.2 g of potassium hydroxide in 90 ml of distilled water, 10.0 g of 4-[1-(4-fluorophenyl)-1H-indazol-3-yl]-1-piperazine carboxylic acid ethyl ester, and 180 ml of methoxyethanol was refluxed for 16 hours and then poured into water. The aqueous mixture was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated to give 6.0 g (75%) of 1-(4-fluorophenyl)-3-(1-piperazinyl)-1H-indazole. Recrystallization from isopropyl ether gave the analytical sample, mp 85°-87°.

Workup

  1. extractionThe aqueous mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9a72e6e70882424cbdd07576a00fbf53
Source dataset
uspto-grants-1992_07
Patent number
US05134236

Reaction notes

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