Ethyl chloroformate → HCID 70514099, compound

HRID 1155616Notes

Reaction equation

HRID 1155616 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].Cl.[Cl:8][C:9]1[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=1)[O:12][C@@H:13]1[CH2:18][CH2:17][N:16](C)[CH2:15][C@H:14]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1>[Cl:8][C:9]1[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=1)[O:12][C@@H:13]1[CH2:18][CH2:17][N:16]([C:2]([O:4][CH2:5][CH3:6])=[O:3])[CH2:15][C@H:14]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformate2×HCID 11430Potassium CarbonateHCID 12788472HCID 12788472, compound

Product 1

HCID 70514099HCID 70514099, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2.01 g of ethyl chloroformate are added to a mixture of 3.7 g of the free base of trans-4-(3-chlorophenoxy)-1-methyl-3-phenylpiperidine of Example 32, 2.56 g of anhydrous potassium carbonate, and 28 ml of dry benzene. The mixture is then refluxed for 18 hours under nitrogen. An additional 0.67 g of ethyl chloroformate is added, and, after 4 more hours of reflux, the mixture is cooled and partitioned between water and ether. The phases are separated and the aqueous phase is extracted with ether. The combined organic phases are washed with saturated aqueous NaCl solution, stirred for 18 hours with anhydrous MgSO4, filtered and concentrated in vacuo to an oil comprising trans-4-(3-chlorophenoxy)-1-ethoxycarbonyl-3-phenylpiperidine.

Workup

  1. temperatureThe mixture is then refluxed for 18 hours under nitrogen
  2. temperatureafter 4 more hours of reflux
  3. temperaturethe mixture is cooled
  4. custompartitioned between water and ether
  5. customThe phases are separated
  6. extractionthe aqueous phase is extracted with ether
  7. washThe combined organic phases are washed with saturated aqueous NaCl solution
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo to an oil

Sources & evidence

ORD record
ord-1e3dbd6b2f0943b0a87935c1c50584fa
Source dataset
uspto-grants-1981_11
Patent number
US04302590

Reaction notes

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