Ammonia → Moclobemide

HRID 2057462Notes

Reaction equation

HRID 2057462 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([NH:8][CH2:9][CH2:10]Cl)=[O:7])=[CH:4][CH:3]=1.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.N>O>[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8083MorpholineHCID 2339784-Chloro-n-(2-chloroethyl)benzamide

Product 1

HCID 4235Moclobemide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.45 G. of p-chloro-N-(2-chloroethyl)-benzamide and 8.7 g. of morpholine are stirred together for 2 hours at 100° C. The mixture is cooled to room temperature and 50 ml. of water are added. Then, the mixture is rendered basic with 10% ammonia solution and extracted three times with 50 ml. of methylene chloride each time. The methylene chloride extract is dried over sodium sulfate and evaporated. The residue is chromatographed over a silica gel column with a mixture of chloroform and ethanol. The product is recrystallized from isopropanol, and 2.2 g. of p-chloro-N-(2-morpholinoethyl)-benzamide are obtained, which is identical to the product obtained in Example 1.

Workup

  1. extractionextracted three times with 50 ml
  2. extractionThe methylene chloride extract
  3. dry with materialis dried over sodium sulfate
  4. customevaporated
  5. customThe residue is chromatographed over a silica gel column with a mixture of chloroform and ethanol
  6. customThe product is recrystallized from isopropanol, and 2.2 g

Sources & evidence

ORD record
ord-cda54c1f1dfb4de780abaac0498a0fd6
Source dataset
uspto-grants-1980_07
Patent number
US04210754

Reaction notes

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