Dimethyl Sulfoxide → 1-Ethyl-4-(6-nitropyridin-3-yl)piperazine

HRID 1918871Notes

Reaction equation

HRID 1918871 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[CH2:11]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[CH3:12].C([O-])([O-])=O.[K+].[K+].CS(C)=O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:11]([N:13]1[CH2:18][CH2:17][N:16]([C:2]2[CH:7]=[N:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:15][CH2:14]1)[CH3:12]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 791961-EthylpiperazineHCID 8176205-Bromo-2-nitropyridine

Product 1

HCID 575020861-Ethyl-4-(6-nitropyridin-3-yl)piperazine

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a sealed tube equipped with a stirring bar, 5-bromo-2-nitropyridine (3.00 g, 14.78 mmol), 1-ethylpiperazine (5.06 g, 44.34 mmol), tetrabutylammonium iodide (273 mmol, 0.739 mmol), K2CO3 (6.128 g, 44.34 mmol), and DMSO (30 mL) were added. The tube was sealed and heated at 90° C. overnight. Water (200 mL) was added and the precipitation was filtered to afford 138a as a yellow solid, 1.24 g.

Workup

  1. customTo a sealed tube equipped with a stirring bar
  2. customThe tube was sealed
  3. customthe precipitation
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-d7f207ea6b8449cc8ded7d5adb697fd0
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

Loading…