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

HRID 1762751Notes

Reaction equation

HRID 1762751 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-360b4bf26ad944559d32d65282900368
Source dataset
uspto-grants-1989_05
Patent number
US04833244

Reaction notes

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