Morpholine → Moclobemide

HRID 2057461Notes

Reaction equation

HRID 2057461 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]2[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][CH2:10][CH2:9][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[O:7])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 2450271-(4-Chlorobenzoyl)aziridine

Product 1

HCID 4235Moclobemide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

55.4 G. of p-chlorobenzoylaziridine and 26.5 g. of morpholine are boiled in 250 ml. of toluene for 2 hours under reflux. The solution is then cooled to room temperature, whereupon crystals separate out. The solution which crystallizes is allowed to stand overnight in a refrigerator. Thereafter, the product is removed by filtration, washed with toluene and recrystallized from isopropanol, and 75.9 g. of p-chloro-N-(2-morpholinoethyl)-benzamide are obtained, which is identical to the product obtained in Example 1.

Workup

  1. customseparate out
  2. customThe solution which crystallizes
  3. customThereafter, the product is removed by filtration
  4. washwashed with toluene
  5. customrecrystallized from isopropanol, and 75.9 g

Sources & evidence

ORD record
ord-6a997b4ee6b14561a49738f88756156d
Source dataset
uspto-grants-1980_07
Patent number
US04210754

Reaction notes

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