Water → HCID 20211979, compound

HRID 1906418Notes

Reaction equation

HRID 1906418 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.Cl.Cl.[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:31])[CH2:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].O>C(O)CC>[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:31])[CH2:22][CH2:23][CH2:24][N:25]2[CH2:26][CH2:27][N:28]([C:4]3[N:3]=[C:2]([NH2:1])[C:7]([NH2:8])=[CH:6][CH:5]=3)[CH2:29][CH2:30]2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 202119871-(4-Fluorophenyl)-4-(piperazin-1-yl)butan-1-one--hydrogen chloride (1/2)

Product 1

HCID 20211979HCID 20211979, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

6 g 2-amino-6-chloro-3-nitropyridine, 12.6 g 1-(4-fluorophenyl)-4-(1-piperazinyl)-1-butanone dihydrochloride and 20 g potassium carbonate in 120 ml n-propanol are stirred under reflux for 21/2 hours. The mixture is then treated with 400 ml water, stirred for further 10 minutes and cooled in an ice bath. The resulting precipitate is filtered off, washed with water, dissolved in methylene chloride, dried over sodium sulphate and evaporated. The resulting 1-(4-fluorophenyl)-4-[4-(2-amino-3-nitro-pyridin-6-yl)-1-piperazinyl]-1-butanone, m.p. 128°-130°, is without further purification dissolved in 400 ml methanol. 3 g palladium on charcoal (5%) are added to the solution and the mixture is hydrogenated under normal conditions. The catalyst is filtered off and the solvent distilled off to give 1-(4-fluorophenyl)-4-[4-(2,3-diaminopyridin-6-yl)-1-piperazinyl]-1-butanone which is used without further purification.

Workup

  1. temperatureunder reflux for 21/2 hours
  2. temperaturecooled in an ice bath
  3. filtrationThe resulting precipitate is filtered off
  4. washwashed with water
  5. dissolutiondissolved in methylene chloride
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. customThe resulting 1-(4-fluorophenyl)-4-[4-(2-amino-3-nitro-pyridin-6-yl)-1-piperazinyl]-1-butanone, m.p. 128°-130°, is without further purification
  9. dissolutiondissolved in 400 ml methanol
  10. addition3 g palladium on charcoal (5%) are added to the solution
  11. filtrationThe catalyst is filtered off
  12. distillationthe solvent distilled off

Sources & evidence

ORD record
ord-19111e5213764faabc7980ac5df3d8d7
Source dataset
uspto-grants-1987_03
Patent number
US04652565

Reaction notes

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