o-Xylyl bromide → N-(2-methylbenzyl)4-piperidone

HRID 1179329Notes

Reaction equation

HRID 1179329 reaction equation
Cl.O.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[CH3:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19]Br>CC#N>[CH3:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][N:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 6992o-Xylyl bromideHCID 11430Potassium CarbonateHCID 2723901Piperonylamine

Product 1

HCID 11959536N-(2-methylbenzyl)4-piperidone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 2.00 g of 4-piperidone monohydrate hydrochloride and 5.40 g of potassium carbonate in 30 ml of CH3CN was added dropwise 1.57 ml of 2-methyl benzyl bromide at 0° C. After stirred at 0° C. or 3.5 h, the mixture was stirred at room temperature for an hour. At 0° C., the mixture was quenched with water and extracted with CHCl3. The organic layer was washed with water, aqueous NaOH, and brine, and dried over anhydrous Na2SO4. The organic solvent was evaporated to give the crude product of 2.52 g of N-(2-methylbenzyl)-4-piperidone as a yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for an hour
  2. customAt 0° C., the mixture was quenched with water
  3. extractionextracted with CHCl3
  4. washThe organic layer was washed with water, aqueous NaOH, and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe organic solvent was evaporated

Sources & evidence

ORD record
ord-26b9fb9c1a1f408b8fd40ab93358bda6
Source dataset
uspto-grants-2007_10
Patent number
US07279490B2

Reaction notes

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