1-(4-chlorobenzoyl)pyrrolidine-2,5-dione → Moclobemide

HRID 2057459Notes

Reaction equation

HRID 2057459 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([N:8]2[C:12](=O)[CH2:11]CC2=O)=[O:7])=[CH:4][CH:3]=1.NCC[N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][CH2:12][CH2:11][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[O:7])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 2403431-(4-chlorobenzoyl)pyrrolidine-2,5-dioneHCID 4082852-Morpholinoethylamine

Product 1

HCID 4235Moclobemide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.4 G. of N-(p-chlorobenzoyl)-succinimide are added to a solution of 1.3 g. of N-(2-aminoethyl)-morpholine in 100 ml. of dioxane and the mixture is stirred overnight at room temperature. The mixture is then evaporated to dryness. 50 Ml. of ice-water are added to the oily residue and the mixture which crystallizes is allowed to stand overnight in a refrigerator. The product is removed by filtration, washed with cold water, dried and recrystallized from isopropanol, and 0.65 g. of p-chloro-N-(2-morpholinoethyl)-benzamide is obtained, which is identical to the product obtained in Example 1.

Workup

  1. customThe mixture is then evaporated to dryness
  2. additionof ice-water are added to the oily residue
  3. customthe mixture which crystallizes
  4. customThe product is removed by filtration
  5. washwashed with cold water
  6. customdried
  7. customrecrystallized from isopropanol, and 0.65 g

Sources & evidence

ORD record
ord-f9bab291382b47d5abe7c5fa99144f21
Source dataset
uspto-grants-1980_07
Patent number
US04210754

Reaction notes

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