Water → 1-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methyloxy)ethyl]piperazine

HRID 419657Notes

Reaction equation

HRID 419657 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7](F)[C:6]([CH3:10])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].[CH3:14][O:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[CH3:10][C:6]1[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[N:21]1[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][O:15][CH3:14])[CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27346381-(2-Methoxyethyl)piperazineHCID 184681411-Fluoro-5-methoxy-2-methyl-4-nitrobenzene

Product 1

HCID 594526231-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methyloxy)ethyl]piperazineYield 86.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

To 1-fluoro-2-methyl-5-(methyloxy)-4-nitrobenzene (prepared according to Example 113, Step B) (1 g, 5.4 mmol) in 10 mL of DMSO was added, 1-[2-(methyloxy)ethyl]piperazine (1 g, 7 mmol), and K2CO3 (1.27 g, 4.2 mmol). The mixture was heated to 130° C. for 24 h. The mixture was then poured into 100 mL of H2O and extracted with EtOAc. The product was isolated by flash chromatography to give the title compound of step A (1.44 g, 4.65 mmol, 86%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.74 (s, 1H), 6.68 (s, 1H), 3.88 (s, 3H), 3.44 (t, J=5.68 Hz, 2H), 3.22 (s, 3H), 2.95-3.01 (m, 4H), 2.50-2.58 (m, 6H), 2.17 (s, 3H).

Workup

  1. extractionextracted with EtOAc
  2. customThe product was isolated by flash chromatography

Sources & evidence

ORD record
ord-3e9e969f373e41a48df7ebb2ef45c5b1
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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