Potassium Carbonate → 1-Isopropyl-4-(5-nitro-pyridin-2-yl)-piperazine

HRID 1783966Notes

Reaction equation

HRID 1783966 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([CH3:13])[CH3:12].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH:11]([N:14]1[CH2:19][CH2:18][N:17]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH2:16][CH2:15]1)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 780131-IsopropylpiperazineHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 339957181-Isopropyl-4-(5-nitro-pyridin-2-yl)-piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-chloro-5-nitropyridine (2.5 g, 15.7 mmol) in THF (25 mL), are added 1-isopropylpiperazine (2.01 g, 15.7 mmol) and K2CO3 (3.25 g, 23.6 mmol). The reaction mixture is stirred at 50° C. for 4 hours and then at 70° C. overnight. The solvent is removed in vacuo and the resultant orange solid is triturated using 10:1 petroleum ether-diethyl ether. The isolated compound (3.7 g, 94%) is used in the next step without further purification.

Workup

  1. customat 70° C.
  2. customovernight
  3. customThe solvent is removed in vacuo
  4. customthe resultant orange solid is triturated
  5. customThe isolated compound (3.7 g, 94%) is used in the next step without further purification

Sources & evidence

ORD record
ord-5b08441a8fae42b5aa4c28a3eb8bc8dc
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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