Ethyl chloroformate → Ethyl 4-(4-fluorobenzoyl)-4-phenylpiperidine-1-carboxylate

HRID 325919Notes

Reaction equation

HRID 325919 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:15][CH2:14][N:13](CC3C=CC=CC=3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[C:29](Cl)(=[O:33])[O:30][CH2:31][CH3:32]>CC1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:15][CH2:14][N:13]([C:29]([O:30][CH2:31][CH3:32])=[O:33])[CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 15586470(4-Fluorophenyl)[4-phenyl-1-(phenylmethyl)-4-piperidinyl]methanone

Product 1

HCID 13477817Ethyl 4-(4-fluorobenzoyl)-4-phenylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred mixture of 79 parts of (4-fluorophenyl)[4-phenyl-1-(phenylmethyl)-4-piperidinyl]methanone and 630 parts of methylbenzene were added dropwise 32 parts of ethyl carbonochloridate at room temperature. Upon completion, stirring was continued for 5 hours at reflux temperature. The reaction mixture was evaporated and the (chloromethyl)benzene was distilled in vacuo (pump). The oily residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2,2'-oxybispropane and a small amount of petroleumether, yielding 35.5 parts of ethyl 4-(4-fluorobenzoyl)-4-phenyl-1-piperidinecarboxylate; mp. 91.7° C. (intermediate 15).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. distillationthe (chloromethyl)benzene was distilled in vacuo (pump)
  4. customThe oily residue was purified by column-chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. customThe residue was crystallized from a mixture of 2,2'-oxybispropane

Sources & evidence

ORD record
ord-f55964ad429f43408a4ec09bf8147188
Source dataset
uspto-grants-1984_04
Patent number
US04443451

Reaction notes

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