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

HRID 359017Notes

Reaction equation

HRID 359017 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-d4108bb2b5044313a3b36123733c6d91
Source dataset
uspto-grants-1991_03
Patent number
US04999356

Reaction notes

Loading…