Water → HCID 14823453, compound

HRID 1955841Notes

Reaction equation

HRID 1955841 reaction equation
[N:1]#[C:2]Br.C[N:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][N:12]=2)[CH2:7][CH2:6]1.O>CS(C)=O>[NH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([N:8]2[CH2:7][CH2:6][N:5]([C:2]#[N:1])[CH2:10][CH2:9]2)=[N:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 10476Cyanogen BromideHCID 148234523-(4-Methylpiperazin-1-yl)-1H-indazole

Product 1

HCID 14823453HCID 14823453, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred mixture of cyanogen bromide (5.3 g, 0.05 mol), K2 CO3 (7.1 g) and dimethylsulfoxide (40 ml) was added, dropwise, 3-(4-methyl-1-piperazinyl)-1H-indazole (1 1.0 g 0.051 mol) dissolved in dimethylsulfoxide (60 ml). The reaction was stirred at ambient temperature for 1 hour, and then it was poured into water. The aqueous suspension was extracted with ethyl acetate, the ethyl acetate was washed (H2O), dried (MgSO4), and concentrated to afford 7.8 g (67%) of a ye llow solid. This sample was combined with another and recrystallized twice from toluene to afford analytically pure 4-(1H-indazol-3-yl)-1-piperazinecarbonitrile as a white solid, m.p.=12°-122° C.

Workup

  1. additionwas added
  2. extractionThe aqueous suspension was extracted with ethyl acetate
  3. washthe ethyl acetate was washed (H2O)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto afford 7.8 g (67%) of a ye llow solid
  7. customrecrystallized twice from toluene

Sources & evidence

ORD record
ord-4aff8aba31e2430a9cf103fa14246ed7
Source dataset
uspto-grants-1998_07
Patent number
US05776963

Reaction notes

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