Sodium hydride → HCID 19020592, compound

HRID 1109483Notes

Reaction equation

HRID 1109483 reaction equation
[C:1]([NH:4][C:5]1[CH:27]=[CH:26][C:8]([C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[CH2:13][CH2:12]2)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[H-].[Na+].[CH2:30](I)[CH2:31][CH3:32]>CN(C=O)C>[C:1]([N:4]([C:5]1[CH:27]=[CH:26][C:8]([C:9]([N:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][C:19]3[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=3)[CH2:15][CH2:16]2)=[O:10])=[CH:7][CH:6]=1)[CH2:30][CH2:31][CH3:32])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 19020597HCID 19020597, compound

Product 1

HCID 19020592HCID 19020592, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

1.7 g of 1-[4-(N-acetylamino)benzoyl]-4-[2-(4-chlorophenyl)ethyl]-piperazine, dissolved in 20 ml DMF, is added to a suspension of 0.23 g 50% NaH in 20 ml DMF. After 1.5 h of stirring at RT, 0.97 g n-propyl iodide, dissolved in 5 ml DMF, are added dropwise. The reaction mixture is stirred overnight. DMF is distilled off in vacuo, water is added, and the product is extracted with ethyl acetate. The organic phase is concentrated by evaporation, and the residue is crystallised from ether/petroleum ether; thus 1-[4-(N-acetyl-N-propylamino)benzoyl]-4-[2-(4-chlorophenyl)ethyl]-piperazine is obtained m.p. 112°-113°.

Workup

  1. additionare added dropwise
  2. stirringThe reaction mixture is stirred overnight
  3. distillationDMF is distilled off in vacuo, water
  4. additionis added
  5. extractionthe product is extracted with ethyl acetate
  6. concentrationThe organic phase is concentrated by evaporation
  7. customthe residue is crystallised from ether/petroleum ether

Sources & evidence

ORD record
ord-9a18c658937c459ea066653b5db43b6b
Source dataset
uspto-grants-1994_06
Patent number
US05321027

Reaction notes

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