Dimethylformamide → 1-Piperazinecarboxamide

HRID 359035

Reaction equation

HRID 359035 reaction equation
[N:1]1([C:7]2C3C(=CC=CC=3)N(C3C=CC(C(F)(F)F)=CC=3)[N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[N+](NC(N)=O)([O-])=[O:27].CN(C)C=O>O>[N:1]1([C:7]([NH2:8])=[O:27])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 62372NitroureaHCID 15117089HCID 15117089, compound

Product 1

HCID 2581921-Piperazinecarboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.5 g of 3-(1-piperazinyl)-1-[4-(trifluoromethyl)phenyl]-1H-indazole, 4.8 g of nitrourea, and 80 ml of dimethylformamide was heated on a steam bath for 15 minutes. The reaction mixture was then poured into water and the resulting precipitate was collected, washed with water, and dried. The precipitate was purified on a Water's Model 500 Preparative High Pressure Liquid Chromatograph (2×) utilizing two silica gel columns and chloroform/methanol (5%) as the eluent. Concentration of the appropriate fractions yielded a solid which was recrystallized from acetonitrile to afford 2.3 g (37%) of 4-[1-(4-trifluoromethyl)phenyl)-1H-indazol-3-yl]-1-piperazine carboxamide, m.p. 138°-140°.

Workup

  1. temperaturewas heated on a steam bath for 15 minutes
  2. customthe resulting precipitate was collected
  3. washwashed with water
  4. customdried
  5. customThe precipitate was purified on a Water'
  6. customConcentration of the appropriate fractions yielded a solid which
  7. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-aad922e3ec3046acb066b31881d3ad15
Source dataset
uspto-grants-1991_03
Patent number
US04999356

Linked notes

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