Water → HCID 14726863, compound

HRID 1646875Notes

Reaction equation

HRID 1646875 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]3[N:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[CH2:15][CH2:14]2)[CH:8]=1)([O-])=O.[BH4-].[Na+].O>C(O)C.O.O.O.O.O.O.[Ni](Cl)Cl>[NH2:1][C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][N:16]([C:19]3[N:20]=[CH:21][CH:22]=[CH:23][N:24]=3)[CH2:17][CH2:18]2)[CH:8]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 11724258HCID 11724258, compound

Product 1

HCID 14726863HCID 14726863, compoundYield 69.5%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 702EthanolSolvent

Procedure

10.2 g (43.2 mmol) of nickel(II) chloride hexahydrate are added to a solution of 7.2 g (21 mmol) of 4-nitro-1-{4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl}-1H-pyrazole, Example no. 7, in 60 ml of ethanol with vigorous stirring. The mixture is cooled in an ice bath and 10.2 g (81 mmol) of sodium borohydride are added slowly. The mixture is left stirring for 1 hour and, after 1 hour at room temperature, water is added, the mixture is evaporated under vacuum, the residue is acidified with concentrated hydrochloric acid and the resulting mixture is filtered, alkalinised with ammonia solution and extracted with ethyl ether. 4.4 g of 4-amino-1-{4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl}-1H-pyrazole are thereby obtained in liquid form.

Workup

  1. temperatureThe mixture is cooled in an ice bath
  2. waitThe mixture is left
  3. customthe mixture is evaporated under vacuum
  4. filtrationthe resulting mixture is filtered
  5. extractionextracted with ethyl ether

Sources & evidence

ORD record
ord-483cb95edd174ad185534339cc2250c5
Source dataset
uspto-grants-1993_01
Patent number
US05182281

Reaction notes

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