Water → HCID 14726863, compound

HRID 373007Notes

Reaction equation

HRID 373007 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.[Ni]>[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 935NickelCatalystHCID 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 4nitro-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 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 mixture is filtered
  5. extractionextracted with ethyl ether

Sources & evidence

ORD record
ord-c3789e8db94d4a468aafbd5b7065bb9a
Source dataset
uspto-grants-1992_11
Patent number
US05162323

Reaction notes

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