Water → 4-(2-Phenylethyl)piperidine

HRID 704386Notes

Reaction equation

HRID 704386 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]2[CH2:14][CH2:13][N:12](C(OCC)=O)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O>Br>[C:1]1([CH2:7][CH2:8][CH:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 962WaterHCID 20074040Ethyl 4-(2-phenylethyl)piperidine-1-carboxylate

Product 1

HCID 43418954-(2-Phenylethyl)piperidineYield 82.8%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 0.70 g of ethyl 4-(2-phenylethyl)piperidine-1-carboxylate in 6 ml of 47% hydrobromic acid was heated under reflux at 100° C. for 6 hours. A small amount of water was added for dissolution of the resultant crystals, the solution was washed with ether, and the aqueous layer was made alkaline with 20% sodium hydroxide. After salting out with sodium chloride, the aqueous layer was extracted with ether. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 0.42 g of 4-(2-phenylethyl)piperidine.

Workup

  1. temperaturewas heated
  2. washthe solution was washed with ether
  3. extractionthe aqueous layer was extracted with ether
  4. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-de54920d9310412a8fd4fe0c56fe3efe
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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