Sodium hydride → HCID 12044043, compound

HRID 1840532Notes

Reaction equation

HRID 1840532 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([N:14]1[CH2:19][CH2:18][NH:17][C:16](=[O:20])[CH2:15]1)(=[O:13])=[O:12].[H-].[Na+].[C:23]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[CH:27][CH:26]=1)#[N:24]>C1COCC1.CN(C=O)C>[C:23]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29][N:17]2[CH2:18][CH2:19][N:14]([S:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)(=[O:13])=[O:12])[CH2:15][C:16]2=[O:20])=[CH:27][CH:26]=1)#[N:24]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 701274-(Chloromethyl)benzonitrileHCID 8321444HCID 8321444, compound

Product 1

HCID 12044043HCID 12044043, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

In THF (8 ml) and DMF (2 ml) was dissolved 4-(naphthalene-2-sulfonyl)-2-piperazinone (290 mg), and to the mixture was added sodium hydride (60% in oil, 40 mg) at 0° C. The mixture was stirred for 20 minutes, to which was added 4-cyanobenzylchloride (182 mg), and the mixture was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried (MgSO4) and concentrated. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:2) to give colorless crystals of the title compound (220 mg).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionTo the residue was added water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-117c13149d1d45e4b9ab9be64d543821
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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