Sodium hydride → 1-n-Butyl-3-(beta-diethylaminoethoxy)-4-phenyl-3-pyrrolin-2-one

HRID 1395669Notes

Reaction equation

HRID 1395669 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8]N(C)[CH2:6][CH2:5]1.[CH2:11]([N:15]1[CH2:19][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:17]([OH:26])[C:16]1=[O:27])[CH2:12][CH2:13][CH3:14].[H-].[Na+].[H][H]>CN(C)C=O>[CH2:11]([N:15]1[CH2:19][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:17]([O:26][CH2:8][CH2:9][N:4]([CH2:3][CH3:2])[CH2:5][CH3:6])[C:16]1=[O:27])[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 4137911-(2-Chloroethyl)-4-methylpiperazine2×HCID 205743601-n-Butyl-3-hydroxy-4-phenyl-3-pyrrolin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 205743411-n-Butyl-3-(beta-diethylaminoethoxy)-4-phenyl-3-pyrrolin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

N1 -β-chloroethyl-N4 -methylpiperazine, 1-n-butyl-3-[N1 -β-(N4 -methyl)-piperazinoethoxy]-4-phenyl-3-pyrrolin-2-one; dioxalate m.p. 199° C. 32.5 g. (0.14 mol) 1-n-butyl-3-hydroxy-4-phenyl-3-pyrrolin-2-one is added, with stirring, at 40° C. to a suspension of 4.2 g. sodium hydride (80%) in 200 ml. dimethyl formamide. When the evolution of hydrogen ceases, 30.0 g. N1 -β-chloroethyl-N4 -methylpiperazine is added and the mixture allowed to react for 30 minutes at 70° C. The mixture is immediately poured into 1.5 liters of ice water. This is then extracted twice with dichloromethane and the organic phase is washed with water. After drying over anhydrous magnesium sulphate, the solvent is distilled off. The residue (base) is taken up in diethyl ether and oxalic acid is added to precipitate out the di-oxalate. After recrystallization of this dioxalate from aqueous methanol, there is obtained 33.0 g. (44% of theory) of the desired end product.

Workup

  1. customto react for 30 minutes at 70° C
  2. extractionThis is then extracted twice with dichloromethane
  3. washthe organic phase is washed with water
  4. dry with materialAfter drying over anhydrous magnesium sulphate
  5. distillationthe solvent is distilled off
  6. additionoxalic acid is added
  7. customto precipitate out the di-oxalate
  8. customAfter recrystallization of this dioxalate from aqueous methanol
  9. customthere is obtained 33.0 g

Sources & evidence

ORD record
ord-480428c9b96742b0925cd1233a064f29
Source dataset
uspto-grants-1980_05
Patent number
US04205078

Reaction notes

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