Water → 1'-[2,5-Bis(methyloxy)-4-nitrophenyl]-1,4'-bipiperidine

HRID 419417Notes

Reaction equation

HRID 419417 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+].[N:21]1([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]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:30]1[CH2:31][CH2:32][CH:27]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH2:28][CH2:29]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 786071,4'-BipiperidineHCID 813621-Chloro-2,5-dimethoxy-4-nitrobenzene

Product 1

HCID 594525701'-[2,5-Bis(methyloxy)-4-nitrophenyl]-1,4'-bipiperidineYield 37.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

4-Chloro-2,5-dimethoxynitrobenzene (5.0 g, 23 mmol) was dissolved in DMSO (50 mL). K2CO3 (4.8 g, 34 mmol) and 4-piperidinopiperidine (3.9 g, 23 mmol) were added and the reaction mixture was heated to 80° C. and allowed to stir over the weekend. 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 A (3.0 g, 37%). MS (M+H, ES+) 350.

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-142f1dd492ad474c92ba7c807ed34124
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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