Formic Acid → 4-formyl-1-(1-phenyl-1H-indazol-3-yl)piperazine

HRID 359031

Reaction equation

HRID 359031 reaction equation
C(O[C:5](=[O:7])C)(=O)C.C(O)=O.[C:11]1([N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[N:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O1CCCC1>[CH:5]([N:29]1[CH2:30][CH2:31][N:26]([C:19]2[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:17]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:18]=2)[CH2:27][CH2:28]1)=[O:7]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 97956441-phenyl-3-(1-piperazinyl)-1H-indazole

Product 1

HCID 151170984-formyl-1-(1-phenyl-1H-indazol-3-yl)piperazineYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.4 ml of acetic anhydride and 1.5 ml of formic acid heated at 55° C. for 1.5 hours and then cooled to ambient temperature was added, dropwise, a solution of 5.6 g of 1-phenyl-3-(1-piperazinyl)-1H-indazole in 20 ml of tetrahydrofuran. The reaction mixture was stirred at ambient temperature for 2 hours and then concentrated to an oil. Trituration of the oil with refluxing diethyl ether yielded a solid which was recrystallized from isopropanol (3×) to yield 2.6 g (42%) of 4-formyl-1-(1-phenyl-1H-indazol-3-yl)piperazine, m.p. 130°-132°.

Workup

  1. additionwas added
  2. concentrationconcentrated to an oil
  3. customTrituration of the oil with refluxing diethyl ether yielded a solid which
  4. customwas recrystallized from isopropanol (3×)

Sources & evidence

ORD record
ord-b6f36608343d49b6acdc80ac0c09f714
Source dataset
uspto-grants-1991_03
Patent number
US04999356

Linked notes

Loading…