Benzene → Moclobemide

HRID 2057463Notes

Reaction equation

HRID 2057463 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[NH2:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C1C=CC=CC=1>O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([NH:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 77264-ChlorobenzaldehydeHCID 4082852-Morpholinoethylamine

Product 1

HCID 4235Moclobemide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

26 G. of p-chlorobenzaldehyde and 24 g. of N-(2-aminoethyl)-morpholine are boiled in 150 ml. of benzene for 3 hours under reflux with water being separated. Then, the mixture is evaporated to dryness and the residue is distilled at 165° C./0.01 mmHg. 5 G. of the resulting 4-{2-[(p-chlorobenzylidene)-amino]-ethyl}-morpholine, 2.3 g. of sodium acetate and 3 ml. of 30% hydrogen peroxide are stirred in 60 ml. of methanol overnight at room temperature. Thereafter, the mixture is evaporated to dryness and the residue is taken up in 50 ml. of methylene chloride and 50 ml. of water. The phases are separated and the aqueous phase extracted with 50 ml. of methylene chloride. 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 pure fractions are combined and evaporated. The residue is recrystallized from isopropanol, and 0.7 g. of p-chloro-N-(2-morpholinoethyl)-benzamide is obtained, which is identical to the product obtained in Example 1.

Workup

  1. customseparated
  2. customThen, the mixture is evaporated to dryness
  3. distillationthe residue is distilled at 165° C./0.01 mmHg
  4. customof methanol overnight
  5. customat room temperature
  6. customThereafter, the mixture is evaporated to dryness
  7. customThe phases are separated
  8. extractionthe aqueous phase extracted with 50 ml
  9. extractionThe methylene chloride extract
  10. dry with materialis dried over sodium sulfate
  11. customevaporated
  12. customThe residue is chromatographed over a silica gel column with a mixture of chloroform and ethanol
  13. customevaporated
  14. customThe residue is recrystallized from isopropanol, and 0.7 g

Sources & evidence

ORD record
ord-63b61b5220684d0599dc13f83608250e
Source dataset
uspto-grants-1980_07
Patent number
US04210754

Reaction notes

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