Potassium Carbonate → HCID 10763979, compound

HRID 1614793Notes

Reaction equation

HRID 1614793 reaction equation
[H-].[Na+].[C:3]1([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Br.[NH:24]1[CH2:29][CH2:28][CH2:27][C@@H:26]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:25]1.C(=O)([O-])[O-].[K+].[K+]>C(OCCCC)CCC.C(OCC)(=O)C>[CH2:33]([O:32][C:30]([C@@H:26]1[CH2:27][CH2:28][CH2:29][N:24]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:25]1)=[O:31])[CH3:34]

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 11487DiphenylamineHCID 123681,6-DibromohexaneHCID 24758Sodium hydrideHCID 185582ethyl (3R)-piperidine-3-carboxylate

Product 1

HCID 10763979HCID 10763979, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 8909Butyl etherSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of sodium hydride (0.7 g, 0.023 mol, 80% oil dispersion) and diphenylamine (3.4 g, 0.020 mol) in dry dibutylether (30 ml) was heated at reflux temperature for 1 h under an atmosphere of nitrogen. The reaction mixture was cooled and 1,6-dibromohexane (3.1 ml) was added. The mixture was heated at reflux temperature for 3 h and then cooled to 40° C. Ethyl (R)-3-piperidinecarboxylate (3.5 g, 0.022 mol) and potassium carbonate (3.1 g, 0.022 mol) were added and the mixture was heated at reflux temperature for 16 h under an atmosphere of nitrogen. Ethyl acetate (50 ml) was added, the mixture was filtered and the solvent was evaporated in vacuo. The residue was submitted to flash chromatography on silica gel (200 g) using a mixture of n-heptane and THF (4:1) as eluent. This provided 3.4 g (42% calculated from diphenylamine) of the title compound as an oil. TLC: rf=0.26 (SiO 2 ; n-heptane/THF=7:3).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 1 h under an atmosphere of nitrogen
  3. temperatureThe reaction mixture was cooled
  4. temperatureThe mixture was heated
  5. temperatureat reflux temperature for 3 h
  6. temperaturethe mixture was heated
  7. temperatureat reflux temperature for 16 h under an atmosphere of nitrogen
  8. filtrationthe mixture was filtered
  9. customthe solvent was evaporated in vacuo
  10. additiona mixture of n-heptane and THF (4:1) as eluent

Sources & evidence

ORD record
ord-9662171897ab489c8c91bb2ef630adc4
Source dataset
uspto-grants-1993_03
Patent number
US05198451

Reaction notes

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