Water → HCID 14032637, compound

HRID 1722154Notes

Reaction equation

HRID 1722154 reaction equation
[N:1]#[C:2]Br.C([O-])([O-])=O.[K+].[K+].Cl.C[N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:19]=2)[CH2:14][CH2:13]1.O>CS(C)=O>[C:27]1([N:20]2[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:18]([CH:15]3[CH2:16][CH2:17][N:12]([C:2]#[N:1])[CH2:13][CH2:14]3)=[N:19]2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 14032585HCID 14032585, compound

Product 1

HCID 14032637HCID 14032637, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a mixture of cyanogen bromide (5.76 g, 0.054 moles) and K2CO3 (8.82 g, 0.064 moles) in dimethylsulfoxide (110 ml) was added 3-(1-methyl-4-piperidinyl)-1-phenyl-1H-indazole (14.8 g, 0.051 moles) of Example 66 in dimethylsulfoxide (DMSO) (15 ml). The reaction was stirred at ambient temperature for 16 hours and then poured into water and extracted with ether. A precipitate formed in the ether which was collected and then the ether was concentrated to yield additional product. The crude product (11.5 g) was crystallized three times from isopropyl alcohol which yielded 6.75 g (37%) of 4-(1-phenyl-1H-indazol-3-yl)piperidine-1-carbonitrile, m.p. 124°-125° C.

Workup

  1. extractionextracted with ether
  2. customA precipitate formed in the ether which
  3. customwas collected
  4. concentrationthe ether was concentrated
  5. customto yield additional product
  6. customThe crude product (11.5 g) was crystallized three times from isopropyl alcohol which

Sources & evidence

ORD record
ord-e394a7c484104d80ad726442cad5dbeb
Source dataset
uspto-grants-1989_08
Patent number
US04853470

Reaction notes

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