Water → 1-{1-[2,5-Bis(methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(2-fluoroethyl)piperazine

HRID 419424Notes

Reaction equation

HRID 419424 reaction equation
Cl[C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[C:4]([O:13][CH3:14])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[F:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][N:27]([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH2:26][CH2:25]1.O>CS(C)=O>[CH3:9][O:8][C:7]1[CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:4]([O:13][CH3:14])=[CH:3][C:2]=1[N:33]1[CH2:32][CH2:31][CH:30]([N:27]2[CH2:26][CH2:25][N:24]([CH2:23][CH2:22][F:21])[CH2:29][CH2:28]2)[CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 813621-Chloro-2,5-dimethoxy-4-nitrobenzeneHCID 594527951-(2-Fluoroethyl)-4-(4-piperidinyl)piperazine

Product 1

HCID 594529191-{1-[2,5-Bis(methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(2-fluoroethyl)piperazineYield 75%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

4-Chloro-2,5-dimethoxynitrobenzene (1.0 g, 4.6 mmol) was dissolved in DMSO (10 mL). K2CO3 (0.953 g, 6.9 mmol) and 1-(2-fluoroethyl)-4-(4-piperidinyl)piperazine (0.989 g, 4.6 mmol) were added and the reaction mixture was heated to 80° C. and allowed to stir for 60 h. The mixture was then poured into H2O and extracted with EtOAc (2×). The combined organics were dried with MgSO4, filtered, and concentrated in vacuo. The resulting residue was adsorbed onto silica gel and flash chromatographed to give the title compound of step E (1.36 g, 75%). MS (M+H, ES+) 397.

Workup

  1. extractionextracted with EtOAc (2×)
  2. dry with materialThe combined organics were dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customchromatographed

Sources & evidence

ORD record
ord-ca07871b5ba04d9c8a437eaba32ff950
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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