Bromide ion → HCID 18782759, compound

HRID 1420709Notes

Reaction equation

HRID 1420709 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:9].[Br-].[C:11]([N:14]1[CH2:19][CH2:18][C:17](=[O:20])[CH2:16][CH2:15]1)(=[O:13])[CH3:12].[NH4+].[Cl-]>C(OCC)C>[C:11]([N:14]1[CH2:19][CH2:18][C:17]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[CH3:9])([OH:20])[CH2:16][CH2:15]1)(=[O:13])[CH3:12]

Participants

7

Reactant 5

HCID 259Bromide ionHCID 72362-Bromotoluene2×HCID 25517Ammonium ChlorideHCID 122563N-Acetyl-4-piperidoneHCID 5462224Magnesium

Product 1

HCID 18782759HCID 18782759, compoundYield 8.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To magnesium turnings (1.82 g, 0.075 mol), covered by dry diethylether (100 mL) under a N2 atmosphere was dropwise added 2-bromotoluene (14.22 g, 0.083 mol). After addition of approximately 1/5 of the bromide the reaction was initiated by gently heating the mixture. The remaining 2-bromotoluene was added over a period of 5 min. When addition was completed the resulting mixture was refluxed for 1.5 h. 1-Acetyl-4-piperidone (9.53 g, 0.068 mol) was added dropwise at ambient temperature and diethylether (100 mL) was added. The reaction mixture was stirred at reflux temperature for 30 min and 1 h at room temperature. 4M NH4Cl (aq) (100 mL) was added and the phases were separated. The organic phase was washed with brine (10 mL), dried (MgSO4) and the solvent evaporated in vacuo. The residual oil was purified on a silica gel column (Eluent: CH2Cl2 /methanol (19:1)) to give the title compound 1.31 g (8%). M.p. 145-146° C.

Workup

  1. temperatureby gently heating the mixture
  2. additionWhen addition
  3. temperaturewas refluxed for 1.5 h
  4. temperatureat reflux temperature for 30 min
  5. custom1 h
  6. customat room temperature
  7. customthe phases were separated
  8. washThe organic phase was washed with brine (10 mL)
  9. dry with materialdried (MgSO4)
  10. customthe solvent evaporated in vacuo
  11. customThe residual oil was purified on a silica gel column (Eluent: CH2Cl2 /methanol (19:1))

Sources & evidence

ORD record
ord-141d05f04ff7416e80058bad55089692
Source dataset
uspto-grants-2000_06
Patent number
US06071932

Reaction notes

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