Potassium Carbonate → 3,5-Dimethyl-1-(3-Methyl-4-Nitrobenzyl)piperidine

HRID 1500174Notes

Reaction equation

HRID 1500174 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5]Br.[CH3:13][CH:14]1[CH2:19][CH:18]([CH3:20])[CH2:17][NH:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:13][CH:14]1[CH2:19][CH:18]([CH3:20])[CH2:17][N:16]([CH2:5][C:4]2[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:2]([CH3:1])[CH:3]=2)[CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1182593,5-DimethylpiperidineHCID 44459783-Methyl-4-nitrobenzyl bromide

Product 1

HCID 533585523,5-Dimethyl-1-(3-Methyl-4-Nitrobenzyl)piperidineYield 61%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Methyl-4-nitrobenzyl bromide (1.00 g), 3,5-dimethylpiperidine (0.60 ml) and potassium carbonate (0.90 g) were dissolved in acetone (20 ml), followed by heating under reflux for 6 hours. The reaction solution was concentrated under reduced pressure, dissolved in chloroform (10 ml), poured into water (100 ml) and extracted with chloroform (50 ml). The organic layer was washed with saturated brine (100 ml), dried over anhydrous sodium sulfate and, after filtration, concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (developing solvent: n-hexane/ethyl acetate=10:1) to obtain the subject compound (NCR-7) (0.70 g, yield 61%) as a yellow oil.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 6 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. dissolutiondissolved in chloroform (10 ml)
  5. additionpoured into water (100 ml)
  6. extractionextracted with chloroform (50 ml)
  7. washThe organic layer was washed with saturated brine (100 ml)
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationafter filtration
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel flash column chromatography (developing solvent: n-hexane/ethyl acetate=10:1)
  12. customto obtain the subject compound (NCR-7) (0.70 g, yield 61%) as a yellow oil

Sources & evidence

ORD record
ord-2b9d2d25a2154c028c5f4e8e61c44dbe
Source dataset
uspto-grants-2015_12
Patent number
US09206125B2

Reaction notes

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