Ethanol → Ethyl 4-(2-fluorophenyl)piperidine-4-carboxylate

HRID 1164358Notes

Reaction equation

HRID 1164358 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:24]#N)[CH2:13][CH2:12][N:11](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:10][CH2:9]1.S(=O)(=O)(O)O.[OH-:31].[NH4+].[CH2:33]([OH:35])[CH3:34]>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:24]([O:35][CH2:33][CH3:34])=[O:31])[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 20511804HCID 20511804, compound

Product 1

HCID 20511806Ethyl 4-(2-fluorophenyl)piperidine-4-carboxylateYield 68.4%

Conditions

Temperature
150 °C

Procedure

A mixture of 35.8 parts of 4-(2-fluorophenyl)-1-(4-methylphenylsulfonyl)-4-piperidinecarbonitrile and 50 parts of a sulfuric acid solution 75% is stirred for 4 hours at about 150° C. 192 Parts of ethanol are added dropwise. Upon completion, stirring is continued for 5 hours at reflux temperature. The reaction mixture is cooled and poured onto crushed ice. The whole is alkalized with ammonium hydroxide and the product is extracted with dichloromethane. The extract is dried, filtered and evaporated, yielding 17.2 parts (68.4%) of ethyl 4-(2-fluorophenyl)-4-piperidinecarboxylate as a residue.

Workup

  1. stirringUpon completion, stirring
  2. waitis continued for 5 hours
  3. temperatureat reflux temperature
  4. temperatureThe reaction mixture is cooled
  5. additionpoured
  6. customonto crushed ice
  7. extractionthe product is extracted with dichloromethane
  8. customThe extract is dried
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-31ab281da44e465ab89ea166468b19f4
Source dataset
uspto-grants-1983_01
Patent number
US04369184

Reaction notes

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