Sodium hydride → HCID 54455304, compound

HRID 1454400Notes

Reaction equation

HRID 1454400 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[C:6]([CH:9]=1)[CH:7]=O.C([N:20]1[CH2:24][CH2:23][CH2:22][C:21]1=[O:25])(=O)C.[H-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[C:6]([CH:9]=1)[CH:7]=[C:22]1[CH2:23][CH2:24][NH:20][C:21]1=[O:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 702662-Pyrrolidinone, 1-acetyl-HCID 43312894HCID 43312894, compound

Product 1

HCID 54455304HCID 54455304, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 9.0 g (40.5 mmol) of 5-Fluoro-2-(4-methyl-piperazin-1-yl)-benzaldehyde and 5.1 g (40.5 mmol) of N-acetylpyrrolidinone in 80 mL of tetrahydrofuran is slowly added to a 0° C. solution of 5.4 g (133.6 mmol) of sodium hydride in 80 mL of tetrahydrofuran over a 2 hour period. After 2.5 hour at 0° C., the reaction is quenched with sat. ammonium chloride and extracted with methylene chloride. The organic layer is dried with magnesium sulfate and concentrated to provide a yellow solid. Recrystallization from ethyl acetate and diispropyl ether provided 3.92 g (33%) of 3-[5-Fluoro-2-(4-methyl-piperazin-1-yl)-benzylidene]-pyrrolidin-2-one as a white solid. Diagnostic C13 NMR (100 MHz, CDCl3) 26.4, 39.9, 46.1, 52.9, 55.3, 115.2, 115.5, 115.8, 116.0, 120.2, 120.3, 126.7, 131.1, 148.9, 157.3, 159.7, 172.8; MS m/z 290.3 (M+1).

Workup

  1. customthe reaction is quenched with sat. ammonium chloride
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic layer is dried with magnesium sulfate
  4. concentrationconcentrated
  5. customto provide a yellow solid
  6. customRecrystallization from ethyl acetate and diispropyl ether

Sources & evidence

ORD record
ord-9a4e210053b74dd59e060c301b6a0e7a
Source dataset
uspto-grants-2009_01
Patent number
US07479559B2

Reaction notes

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