Phenethyl bromide → 3-Butyl-1-(2-phenylethyl)piperidin-4-one

HRID 2245332Notes

Reaction equation

HRID 2245332 reaction equation
[CH2:1]([CH:5]1[C:10](=[O:11])[CH2:9][CH2:8][NH:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].CCN(C(C)C)C(C)C.Br[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C.CCOCC>[CH2:1]([CH:5]1[C:10](=[O:11])[CH2:9][CH2:8][N:7]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 7666Phenethyl bromideHCID 81531DiisopropylethylamineHCID 53417508HCID 53417508, compound

Product 1

HCID 686856063-Butyl-1-(2-phenylethyl)piperidin-4-oneYield 85%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-Butyl-piperidine-4-one (250 mg) in DMF (5 ml) was added DIPEA (468 mg) and then a solution of (2-bromoethyl)-benzene (373 mg) in DMF (5 ml) over a period of 45 min. The resulting mixture was stirred at RT for 1 hour and then heated to 60° C. for 6 hours. The reaction mixture was cooled, diluted with ether and the organic solution was washed with 10% aq. Na2CO3 solution twice and brine. The organic layer was dried over MgSO4, filtered and evaporated to give a residue which was purified by flash chromatography (ethyl acetate/hexanes 1:3) to give the product as a colorless liquid (355 mg). MS (ESI): 260.4 (MH+).

Workup

  1. temperatureheated to 60° C. for 6 hours
  2. temperatureThe reaction mixture was cooled
  3. washthe organic solution was washed with 10% aq. Na2CO3 solution twice
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a residue which
  8. customwas purified by flash chromatography (ethyl acetate/hexanes 1:3)

Sources & evidence

ORD record
ord-4d01222cf93d4c4299adf3e5881729a9
Source dataset
uspto-grants-2010_03
Patent number
US07683079B2

Reaction notes

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