Water → HCID 15117094, compound

HRID 655029Notes

Reaction equation

HRID 655029 reaction equation
[N:1]#[C:2]Br.C(=O)([O-])[O-].[K+].[K+].[C:10]1([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([N:25]3[CH2:30][CH2:29][N:28](C)[CH2:27][CH2:26]3)=[N:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O>CS(C)=O>[C:10]1([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([N:25]3[CH2:30][CH2:29][N:28]([C:2]#[N:1])[CH2:27][CH2:26]3)=[N:17]2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 15117075HCID 15117075, compound

Product 1

HCID 15117094HCID 15117094, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred mixture of 1.5 g of cyanogen bromide 2.0 g of potassium carbonate and 30 ml of dimethylsulfoxide was added, dropwise, a solution of 2.8 g of 1-phenyl-3-(4-methyl-1-piperazinyl)-1H-indazole in 30 ml of dimethylsulfoxide. The reaction mixture was stirred at ambient temperature for 1.5 hours and then poured into water. The aqueous mixture was extracted with ethyl acetate, and the extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated. The concentrate was purified by flash chromatography on silica gel, utilizing ethyl acetate-hexane (1:1) as the eluent, followed by recrystallization from isopropyl alcohol-water to yield 2.3 g (59%) of 4-(1-phenyl-1H-indazol-3-yl)-1-piperazine carbonitrile, m.p. 118°-120°.

Workup

  1. additionwas added
  2. extractionThe aqueous mixture was extracted with ethyl acetate
  3. washthe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash chromatography on silica gel
  7. customfollowed by recrystallization from isopropyl alcohol-water

Sources & evidence

ORD record
ord-b9ba11d744324dc88e6fa5bf716758ed
Source dataset
uspto-grants-1992_07
Patent number
US05134236

Reaction notes

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