Potassium Carbonate → HCID 8054225, compound

HRID 1682545Notes

Reaction equation

HRID 1682545 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][CH2:11]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:13]([O:15][C:16]([C@@H:18]1[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]1)=[O:17])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CC(CC(C)C)=O>[CH2:13]([O:15][C:16]([C@@H:18]1[CH2:23][CH2:22][CH2:21][N:20]([CH2:11][CH2:10][CH2:9][CH2:8][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:19]1)=[O:17])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70986(4-Bromobutoxy)benzeneHCID 185582ethyl (3R)-piperidine-3-carboxylate

Product 1

HCID 8054225HCID 8054225, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 4-phenoxy-1-butylbromide (10 g, 44 mmol), (R)-3-piperidine-carboxylic acid ethyl ester (15 g, 44 mmol), potassium carbonate (18 g, 131 mmol) and methyl isobutylketone (100 ml) was heated at reflux overnight. The reaction mixture was allowed to cool and then filtered. The solvent was evaporated from the filtrate in vacuo and the residue was purified by column chromatography on silica gel (300 g, heptane/ethyl acetate=4/1) to give 12.1 g of (R)-1-(4-phenoxy-1-butyl)-3-piperidinecarboxylic acid ethyl ester as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureto cool
  4. filtrationfiltered
  5. customThe solvent was evaporated from the filtrate in vacuo
  6. customthe residue was purified by column chromatography on silica gel (300 g, heptane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-ebf58c8cbe9c41e3a7d736302b4ac8fd
Source dataset
uspto-grants-1997_06
Patent number
US05635518

Reaction notes

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