Ethyl chloroformate → HCID 15124805, compound

HRID 466544Notes

Reaction equation

HRID 466544 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-cf80821d2bec4a11b2658cb04ae36345
Source dataset
uspto-grants-1992_10
Patent number
US05157035

Reaction notes

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