Butyl bromide → HCID 18318112, compound

HRID 2360586Notes

Reaction equation

HRID 2360586 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+].Br[CH2:19][CH2:20][CH2:21][CH3:22]>C(O)C>[CH2:19]([C:4]1([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2][NH:1][CH2:11][CH2:10]1)[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 18318112HCID 18318112, compoundYield 113.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl isonipecotate (31.8 mmol; 5.0 g), anhydrous potassium carbonate (63.6 mmol; 8.8 g) and 1-bromobutane (31.8 mmol; 4.36 g) in absolute ethanol (63 ml) was stirred at reflux for 3 hours. After cooling, the carbonate was removed by filtration and the filtrate evaporated under reduced pressure. 7.68 g of ethyl 4-butylisonipecotate were obtained in the form of an oil, which was used for the following reaction without further purification. This product was dissolved in anhydrous ethyl ether (32 ml) and added dropwise to a suspension of lithium aluminium hydride (41.3 mmol; 1.57 g) in the same solvent (20 ml) cooled to 0° C. The reaction mixture was stirred at room temperature for 15 hours. After cooling to 0° C., ice was added cautiously and the hydroxides thus formed were removed by filtration. After separating the two phases, the ether phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure to give 5.1 g (94%) of final compound as a clear oil.

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureAfter cooling
  3. customthe carbonate was removed by filtration
  4. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-0791464398044b108a3aecb3ef7a14ec
Source dataset
uspto-grants-2014_04
Patent number
US08686147B2

Reaction notes

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