Benzene → HCID 70513668, compound

HRID 851012Notes

Reaction equation

HRID 851012 reaction equation
C(O)(=O)/C=C\C(O)=O.C[N:10]1[CH2:15][CH2:14][C@@H:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[C@H:12]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:11]1.C(=O)([O-])[O-].[K+].[K+].C1C=CC=CC=1.Cl[C:45]([O:47][CH2:48][CH3:49])=[O:46]>CCOCC.O>[CH2:48]([O:47][C:45]([N:10]1[CH2:15][CH2:14][C@@H:13]([O:16][C:17]2[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=2)[C@H:12]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:11]1)=[O:46])[CH3:49]

Participants

7

Reactant 4

HCID 241BenzeneHCID 10928Ethyl chloroformate2×HCID 11430Potassium CarbonateHCID 12788400HCID 12788400, compound

Product 1

HCID 70513668HCID 70513668, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3.63 g of the free base of Example 3, 1.6 g of anhydrous potassium carbonate and 25 ml of anhydrous benzene is treated with 1.22 ml of ethyl chloroformate, and the mixture is allowed to reflux 18 hours under nitrogen. Then another 0.44 ml of ethyl chloroformate is added and the mixture is refluxed 18 hours, then poured into a mixture of 100 ml of water and 100 ml of ether. The aqueous phase is extracted with ether. The combined ether extracts are washed with water and saturated aqueous NaCl solution, dried over Na2SO4, filtered and concentrated in vacuo to a gum. This material is chromatographed on silica gel, using chloroform as solvent. A fraction of pure material and two fractions of slightly less pure material are obtained. The product of trans-1-ethoxycarbonyl-4-(4-nitrophenoxy)-3-phenylpiperidine is obtained as a glass.

Workup

  1. temperatureto reflux 18 hours under nitrogen
  2. temperaturethe mixture is refluxed 18 hours
  3. extractionThe aqueous phase is extracted with ether
  4. washThe combined ether extracts are washed with water and saturated aqueous NaCl solution
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a gum
  8. customThis material is chromatographed on silica gel
  9. customA fraction of pure material and two fractions of slightly less pure material are obtained

Sources & evidence

ORD record
ord-d8f439e864a241b881c1cb1c53d770de
Source dataset
uspto-grants-1983_05
Patent number
US04382141

Reaction notes

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