Potassium Carbonate → HCID 67106739, compound

HRID 1910790Notes

Reaction equation

HRID 1910790 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:8][CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25]>CN(C=O)C>[CH2:24]([CH:23]([N:13]1[CH2:12][CH2:11][N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=2)[CH2:15][CH2:14]1)[CH2:26][CH3:27])[CH3:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 157383-BromopentaneHCID 29287991-(5-Nitropyridin-2-yl)piperazine

Product 1

HCID 67106739HCID 67106739, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1-(5-nitro-pyridin-2-yl)-piperazine (2.2 g, 10.5 mmol) in DMF (10 mL) were added potassium carbonate (2.9 g, 21 mmol) and 3-bromopentane (4.8 g, 31.7 mmol). The mixture was heated at 120° C. for six hours. DMF was removed in vacuo to give a residue which was partitioned between water and DCM. The organic phase was washed with brine, dried over sodium sulfate and concentrated to give 1-(1-ethyl-propyl)-4-(5-nitro-pyridin-2-yl)-piperazine (550 mg, 19%) as a yellow solid.

Workup

  1. customDMF was removed in vacuo
  2. customto give a residue which
  3. customwas partitioned between water and DCM
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7966927c22774e87b250c2aa7c297cda
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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