1-Isopropylpiperazine → 1-Isopropyl-4-(6-nitropyridin-3-yl)piperazine

HRID 1431100Notes

Reaction equation

HRID 1431100 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[CH:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([CH3:13])[CH3:12]>CS(C)=O.O>[CH:11]([N:14]1[CH2:19][CH2:18][N:17]([C:2]2[CH:7]=[N:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:16][CH2:15]1)([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 780131-IsopropylpiperazineHCID 8176205-Bromo-2-nitropyridine

Product 1

HCID 575020971-Isopropyl-4-(6-nitropyridin-3-yl)piperazineYield 64%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To 5-bromo-2-nitropyridine (1.0 g, 4.93 mmol, Eq: 1.00) in DMSO (10.0 ml) was added 1-isopropylpiperazine (632 mg, 4.93 mmol, Eq: 1.00), and the resulting solution was heated at 70° C. for 18 hours. The solution was cooled to room temperature. The solution was diluted with 50 ml water. The resulting solid was filtered. The solid was washed with water and dried under vacuum. The crude material was purified by flash chromatography (silica gel, 80 g, 0% to 3% MeOH/DCM gradient) to give 1-isopropyl-4-(6-nitropyridin-3-yl)piperazine (788 mg, 64%). LC/MS-ESI observed [M+H]+ 251.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationThe resulting solid was filtered
  3. washThe solid was washed with water
  4. customdried under vacuum
  5. customThe crude material was purified by flash chromatography (silica gel, 80 g, 0% to 3% MeOH/DCM gradient)

Sources & evidence

ORD record
ord-6dbc2894e6e94645add474232b9618a8
Source dataset
uspto-grants-2015_01
Patent number
US08940741B2

Reaction notes

Loading…