Ethanol → 3-Carboxy-4-(4-fluorophenyl)piperidine-6-one

HRID 2084609Notes

Reaction equation

HRID 2084609 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][CH2:10]C2CCC(O)=O)=[CH:4][CH:3]=1.[OH-:20].[Na+].[CH2:22]([OH:24])[CH3:23]>>[C:22]([CH:23]1[CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:13][C:12](=[O:14])[NH:11][CH2:10]1)([OH:20])=[O:24]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 14798Sodium HydroxideHCID 227338414-(4-Fluorophenyl)-3-carboxyethylpiperidin-6-one

Product 1

HCID 226439843-Carboxy-4-(4-fluorophenyl)piperidine-6-one

Procedure

A solution of 4-(4-fluorophenyl)-3-carboxyethylpiperidin-6-one (2.0 g, 0.0075 mol) in ethanol (10 ml) was added to a solution of sodium hydroxide (0.4 g, 0.01 mol) in 95% ethanol and the mixture brought to reflux and stirred for 2.5 hours. The solvent was then removed by evaporation at reduced pressure, and the residue neutralized with 10% aqueous hydrochloric acid (25 ml) and extracted with ethyl acetate (3×20 ml). After separation, the combined organic phases were dried with anhydrous sodium sulphate, filtered. and evaporated to give only 0.1 g of a white solid. The aqueous phase was therefore lyophilized and the residue extracted with hot methanol. The residue, consisting of inorganic salts, was discarded while the methanol extracts were combined and evaporated at reduced pressure to give the title compound (1.34 g, 75%).

Workup

  1. temperatureto reflux
  2. customThe solvent was then removed by evaporation at reduced pressure
  3. extractionthe residue neutralized with 10% aqueous hydrochloric acid (25 ml) and extracted with ethyl acetate (3×20 ml)
  4. customAfter separation
  5. dry with materialthe combined organic phases were dried with anhydrous sodium sulphate
  6. filtrationfiltered
  7. customand evaporated

Sources & evidence

ORD record
ord-8a174a27fb5d4568a89b10d8f77be972
Source dataset
uspto-grants-2004_04
Patent number
US06716985B2

Reaction notes

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