Phenethyl bromide → HCID 10106733, compound

HRID 2360587Notes

Reaction equation

HRID 2360587 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[C:18]1([CH2:24][CH2:25]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O.O>[C:18]1([CH2:24][CH2:25][C:4]2([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2][NH:1][CH2:11][CH2:10]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 10106733HCID 10106733, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of ethyl isonipecotate (64 mmol; 10.0 g), anhydrous potassium carbonate (192 mmol; 26.5 g) and phenylethyl bromide (77 mmol, 14.25 g) in anhydrous N,N-dimethylformamide (100 ml) was stirred at 70° C. for 5 hours 30 minutes. After cooling, the reaction mixture was diluted with water (300 ml) and extracted with ethyl acetate (3×200 ml). The combined organic phases were washed with saturated NaCl solution (3×100 ml), dried over sodium sulfate and evaporated under reduced pressure. A crude product was obtained, which was purified on a column of alumina (eluting with 2/1 n-hexane/ethyl acetate) to give 14.0 g (84%) of pure product as a yellow oil.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (3×200 ml)
  3. washThe combined organic phases were washed with saturated NaCl solution (3×100 ml)
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customA crude product was obtained
  7. customwhich was purified on a column of alumina (eluting with 2/1 n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-15f468eacc54423f82343dd6eb827709
Source dataset
uspto-grants-2014_04
Patent number
US08686147B2

Reaction notes

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