3-Bromotoluene → HCID 22753913, compound

HRID 2163136Notes

Reaction equation

HRID 2163136 reaction equation
[Mg].Br[C:3]1[CH:4]=[C:5]([CH3:9])[CH:6]=[CH:7][CH:8]=1.[CH3:10][N:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1.[Cl-].[NH4+]>CCOCC>[CH3:10][N:11]1[CH2:16][CH2:15][C:14]([C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[CH:4]=2)([OH:17])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 115603-BromotolueneHCID 25517Ammonium ChlorideHCID 740491-Methyl-4-piperidoneHCID 5462224Magnesium

Product 1

HCID 22753913HCID 22753913, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a layer of magnesium (24.3 g) covered with dry ether, a solution of m-bromotoluene (171 g, 1 mole) in dry ether (500 ml) is added under an atmosphere of nitrogen. After the addition, the mixture is heated at reflux for an hour, cooled to 0° C. and a solution of 1-methyl-4-piperidone (108 g, 950 mmoles) is added dropwise to the mechanically stirred mixture. The mixture is heated at reflux for 3 hours and allowed to stand at room temperature overnight. The suspension is cooled (<5°), 10% ammonium chloride solution is added and the mixture is extracted with ether. The combined extracts are dried (MgSO4) and evaporated. The residue is crystallized from hexane to give the title compound, mp 86°-90° C.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture is heated
  3. temperatureat reflux for an hour
  4. temperatureThe mixture is heated
  5. temperatureat reflux for 3 hours
  6. additionis added
  7. extractionthe mixture is extracted with ether
  8. dry with materialThe combined extracts are dried (MgSO4)
  9. customevaporated
  10. customThe residue is crystallized from hexane

Sources & evidence

ORD record
ord-b9e9422bcbeb4412af04c4ebe7323fab
Source dataset
uspto-grants-1979_01
Patent number
US04132710

Reaction notes

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