Ethyl chloroformate → HCID 15124805, compound

HRID 359412Notes

Reaction equation

HRID 359412 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([OH:21])[CH2:13][CH2:12][CH2:11][N:10](CC3C=CC=CC=3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[C:22](Cl)(=[O:26])[O:23][CH2:24][CH3:25]>CC1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([OH:21])[CH2:13][CH2:12][CH2:11][N:10]([C:22]([O:23][CH2:24][CH3:25])=[O:26])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 15124800HCID 15124800, compound

Product 1

HCID 15124805HCID 15124805, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 13 parts of 3-(3-chlorophenyl)-1-(phenylmethyl)-3-piperidinol in 270 parts of methylbenzene were added dropwise 10.9 parts of ethyl carbonochloridate at room temperature. Upon completion, stirring was continued overnight at reflux temperature. After cooling to room temperature, the whole was washed with water and hydrochloric acid. The organic layer was dried, filtered and evaporated, yielding 7 parts (58%) of ethyl 3-(3-chlorophenyl)-3-hydroxy-1-piperidinecarboxylate as a residue (intermediate 50).

Workup

  1. temperatureat reflux temperature
  2. washthe whole was washed with water and hydrochloric acid
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-90fa413a2c5043d9bbbeb4a2d20c1c39
Source dataset
uspto-grants-1991_03
Patent number
US05001125

Reaction notes

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