Hydrochloric Acid → 4-(2-Fluorobenzoyl)-4-hydroxypiperidine

HRID 3970Notes

Reaction equation

HRID 3970 reaction equation
C([N:4]1[CH2:9][CH2:8][C:7]([C:11](=[O:19])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])([OH:10])[CH2:6][CH2:5]1)(=O)C.Cl.[OH-].[Na+]>C(Cl)Cl>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:11]([C:7]1([OH:10])[CH2:6][CH2:5][NH:4][CH2:9][CH2:8]1)=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 138001421-Acetyl-4-(2-fluorobenzoyl)-4-hydroxypiperidine

Product 1

HCID 138001434-(2-Fluorobenzoyl)-4-hydroxypiperidineYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 13.3 g of 1-acetyl-4-(2-fluorobenzoyl)-4-hydroxypiperidine and 20 ml of 6N hydrochloric acid was stirred at reflux under nitrogen for 4 hrs. The reaction mixture was allowed to cool and poured onto ca. 100 g of ice. Methylene chloride was added, and the separated aqueous layer was made strongly basic by means of 15% sodium hydroxide solution. The aqueous layer was extracted three times with 80 ml of methylene chloride. The extracts were dried over anhydrous potassium carbonate, filtered and evaporated provide anhydrous 9.5 g (85%) of product, mp 133°-135° C.

Workup

  1. temperatureat reflux under nitrogen for 4 hrs
  2. temperatureto cool
  3. extractionThe aqueous layer was extracted three times with 80 ml of methylene chloride
  4. dry with materialThe extracts were dried over anhydrous potassium carbonate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-f8752192ea4e4df79d4fa06a0098bd68
Source dataset
uspto-grants-1988_02
Patent number
US04723009

Reaction notes

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