Ethyl chloroformate → (4-Fluorophenyl)(4-hydroxypiperidin-4-yl)methanone--hydrogen chloride (1/1)

HRID 2397471Notes

Reaction equation

HRID 2397471 reaction equation
C([O:4][C:5]1([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:10][CH2:9][N:8](C)[CH2:7][CH2:6]1)(=O)C.[Cl:21]C(OCC)=O>C1C=CC=CC=1>[ClH:21].[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]([C:5]2([OH:4])[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)=[O:20])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 21438446HCID 21438446, compound

Product 1

HCID 21435119(4-Fluorophenyl)(4-hydroxypiperidin-4-yl)methanone--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 27.9 grams (0.1 mole) of 4-acetoxy-4-(p-fluorobenzoyl)-1-methylpiperidine in 200 ml. of benzene was added 27.1 (0.25 mole) of ethyl chloroformate. The mixture was refluxed for 48 hours. The mixture was extracted with H2O, the organic solution was dried (MgSO4) and filtered. The filtrate was concentrated. To the resulting oil was added 250 ml. of 6 Normal HCl and the mixture was refluxed for seventy-two hours. Most of the water was removed under reduced pressure. Ethanol was added and the solution cooled. The solid which precipitated was collected by filtration and recrystallized from ethanol giving eighteen grams of 4-(p-fluorobenzoyl)-4-hydroxypiperidine hydrochloride. Melting point 241°-243° C.

Workup

  1. temperatureThe mixture was refluxed for 48 hours
  2. extractionThe mixture was extracted with H2O
  3. dry with materialthe organic solution was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. additionTo the resulting oil was added 250 ml
  7. temperatureof 6 Normal HCl and the mixture was refluxed for seventy-two hours
  8. customMost of the water was removed under reduced pressure
  9. additionEthanol was added
  10. temperaturethe solution cooled
  11. customThe solid which precipitated
  12. filtrationwas collected by filtration
  13. customrecrystallized from ethanol giving eighteen grams of 4-(p-fluorobenzoyl)-4-hydroxypiperidine hydrochloride

Sources & evidence

ORD record
ord-6c5d9db3dbc44eb38243c8bfa9e9174d
Source dataset
uspto-grants-1977_05
Patent number
US04021564

Reaction notes

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