Sodium hydride → HCID 70984334, compound

HRID 928042Notes

Reaction equation

HRID 928042 reaction equation
[H-].[Na+].[CH2:3]([N:5]1[CH2:10][CH2:9][NH:8][C:7](=[O:11])[CH2:6]1)[CH3:4].[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16]Br>C1COCC1.O.C(OCC)(=O)C>[CH2:3]([N:5]1[CH2:10][CH2:9][N:8]([CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([F:12])[CH:14]=2)[C:7](=[O:11])[CH2:6]1)[CH3:4]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 680073-Fluorobenzyl bromideHCID 17769794HCID 17769794, compound2×

Product 1

HCID 70984334HCID 70984334, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% oil dispersion, 0.176 g) was added to a stirred solution of 4-ethyl-piperazin-2-one (Intermediate 176, 0.512 g) in anhydrous THF (10 mL) and the mixture was stirred at room temperature for 10 minutes. 3-Fluorobenzyl bromide (0.827 g) was added and stirring was continued for 2 hours. The solution was diluted with water and ethyl acetate and the organic layer was dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM with a gradient of 0-5% to give 4-ethyl-1-(3-fluorobenzyl)piperazin-2-one (0.595 g) as a colourless oil.

Workup

  1. stirringstirring
  2. waitwas continued for 2 hours
  3. dry with materialthe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by chromatography on silica
  7. washeluting with a mixture of methanol and DCM with a gradient of 0-5%

Sources & evidence

ORD record
ord-733439e58a254ea29b8c42eb62f7dff3
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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