Water → 1-Methyl-4-[5-nitro-4-(propan-2-yloxy)pyridin-2-yl]piperazine

HRID 518829Notes

Reaction equation

HRID 518829 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.Cl[C:15]1[CH:20]=[C:19]([O:21][CH:22]([CH3:24])[CH3:23])[C:18]([N+:25]([O-:27])=[O:26])=[CH:17][N:16]=1.O>CS(C)=O>[CH3:7][N:8]1[CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[C:19]([O:21][CH:22]([CH3:23])[CH3:24])[C:18]([N+:25]([O-:27])=[O:26])=[CH:17][N:16]=2)[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 866979922-Chloro-4-isopropoxy-5-nitropyridine

Product 1

HCID 866979951-Methyl-4-[5-nitro-4-(propan-2-yloxy)pyridin-2-yl]piperazineYield 92.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
105 °C

Procedure

383 mg of potassium carbonate and 185 mg of 1-methylpiperazine are added to a solution of 400 mg of 2-chloro-5-nitro-4-(propan-2-yloxy)pyridine in 3.7 ml of DMSO. The reaction medium is heated for 1 hour at 105° C. After cooling, the mixture is run into water, extracted with ethyl acetate, washed with a saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue is taken up in diisopropyl ether, and the insoluble material is filtered off and dried under vacuum, so as to give 481 mg of 1-methyl-4-[5-nitro-4-(propan-2-yloxy)pyridin-2-yl]piperazine in the form of an orangey-coloured solid.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washwashed with a saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. filtrationthe insoluble material is filtered off
  8. customdried under vacuum

Sources & evidence

ORD record
ord-a96f2e77c6e045a388f26e8300fd1a12
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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