Water → HCID 23614758, compound

HRID 1768131Notes

Reaction equation

HRID 1768131 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])=[CH:4][CH:3]=1.[F:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18]Br.C(=O)([O-])[O-].[K+].[K+].O>CC(=O)CC.C(OCC)(=O)C>[F:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][O:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 680073-Fluorobenzyl bromideHCID 7855861-(4-hydroxyphenyl)pyrrolidin-2-one

Product 1

HCID 23614758HCID 23614758, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2.73 g (15.4 mmol) of 1-(4-hydroxy-phenyl)-pyrrolidin-2-one, 3.2 g (16.9 mmol) of 3-fluorobenzylbromide and 4.26 g (31 mmol) of potassium carbonate in 100 ml of 2-butanone is heated at 80° C. for 18 hours. After cooling to RT, the reaction mixture is treated with water and ethyl acetate. The organic layer is separated, dried over magnesium sulfate and evaporated under reduced pressure. The solid residue is crystallised from ether to yield 3.86 g (88% of theory) of 1-[4-(3-fluoro-benzyloxy)-phenyl]-pyrrolidin-2-one as a colorless solid. MS: m/e=286.0 (M+H)+.

Workup

  1. temperatureAfter cooling to RT
  2. customThe organic layer is separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe solid residue is crystallised from ether

Sources & evidence

ORD record
ord-bfaab34fd87d4736bf247b26c428ce39
Source dataset
uspto-grants-2007_06
Patent number
US07235581B2

Reaction notes

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