Ethyl chloroformate → HCID 12788499, compound

HRID 1855912Notes

Reaction equation

HRID 1855912 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C@@H:7]2[CH2:12][CH2:11][N:10](C)[CH2:9][C@H:8]2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:29]([O:31][CH2:32][CH3:33])=[O:30]>C1C=CC=CC=1>[CH2:32]([O:31][C:29]([N:10]1[CH2:11][CH2:12][C@@H:7]([O:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:21][CH:20]=2)[C@H:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9]1)=[O:30])[CH3:33]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 12788467HCID 12788467, compound

Product 1

HCID 12788499HCID 12788499, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 3.49 g of trans-4-(4-fluorophenoxy)-1-methyl-3-phenylpiperidine of Example 30, 2.53 g of anhydrous potassium carbonate, and 28 ml of dry benzene are treated all at once under a nitrogen atmosphere with 1.75 ml of ethyl chloroformate. After 1 hour at ambient temperature, the mixture is refluxed 18 hours, then cooled and partitioned between ether and water. The phases are separated and the aqueous phase is extracted with ether. The combined ether extracts are washed with 2 N HCl solution, then with saturated aqueous NaCl solution, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to a gum which eventually crystallizes to a solid of trans-1-ethoxycarbonyl-4-(4-fluorophenoxy)-3-phenylpiperidine, m.p. s 78°, 80°-82.5° C.

Workup

  1. temperaturethe mixture is refluxed 18 hours
  2. temperaturecooled
  3. custompartitioned between ether and water
  4. customThe phases are separated
  5. extractionthe aqueous phase is extracted with ether
  6. washThe combined ether extracts are washed with 2 N HCl solution
  7. dry with materialwith saturated aqueous NaCl solution, dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo to a gum which
  10. customeventually crystallizes to a solid of trans-1-ethoxycarbonyl-4-(4-fluorophenoxy)-3-phenylpiperidine
  11. customs 78°, 80°-82.5° C.

Sources & evidence

ORD record
ord-1c28f2f5eab4451d9dad1d68fcefce03
Source dataset
uspto-grants-1980_08
Patent number
US04216218

Reaction notes

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