Ethyl chloroformate → HCID 70531549, compound

HRID 851041Notes

Reaction equation

HRID 851041 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[O:6][C@@H:7]1[CH2:12][CH2:11][N:10](C)[CH2:9][C@H:8]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:30]([O:32][CH2:33][CH3:34])=[O:31]>C1C=CC=CC=1>[CH2:33]([O:32][C:30]([N:10]1[CH2:11][CH2:12][C@@H:7]([O:6][C:5]2[CH:20]=[CH:21][CH:22]=[C:3]([O:2][CH3:1])[CH:4]=2)[C@H:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9]1)=[O:31])[CH3:34]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformate2×HCID 11430Potassium CarbonateHCID 12788506HCID 12788506, compound

Product 1

HCID 70531549HCID 70531549, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 0.45 g of trans-4-(3-methoxyphenoxy)-1-methyl-3-phenylpiperidine, 0.31 g of anhydrous potassium carbonate, 0.22 ml of ethyl chloroformate and 4 ml of anhydrous benzene is stirred for a few minutes at room temperature, then refluxed overnight. Another 0.11 ml of ethyl chloroformate is added, the mixture is refluxed for another 4 hours, then cooled and partitioned between 25 ml of ether and 25 ml of water. The aqueous phase is extracted with another 25 ml of ether, and the combined ether extracts are washed with 2 N hydrochloric acid (2×10 ml), saturated sodium chloride solution (25 ml), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 0.37 g of product as a yellow oil.

Workup

  1. temperaturerefluxed overnight
  2. temperaturethe mixture is refluxed for another 4 hours
  3. temperaturecooled
  4. custompartitioned between 25 ml of ether and 25 ml of water
  5. extractionThe aqueous phase is extracted with another 25 ml of ether
  6. washthe combined ether extracts are washed with 2 N hydrochloric acid (2×10 ml), saturated sodium chloride solution (25 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5cd11e43906548e3b7d5fc556e3aa1c4
Source dataset
uspto-grants-1983_05
Patent number
US04382141

Reaction notes

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