4-Chlorobenzoyl chloride → Moclobemide

HRID 2057454Notes

Reaction equation

HRID 2057454 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 4082852-Morpholinoethylamine

Product 1

HCID 4235Moclobemide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

35 G. of p-chlorobenzoyl chloride are added dropwise to a solution of 26 g. of N-(2-aminoethyl)-morpholine in 200 ml. of pyridine, while stirring and cooling with ice-water. Thereafter, the mixture is stirred overnight at room temperature and subsequently evaporated to dryness. Then, the residue is evaporated twice more with 200 ml. of toluene each time. The solid residue is taken up in 300 ml. of ice-water and 300 ml. of methylene chloride and rendered basic with 3-N sodium hydroxide solution. The phases are separated and the methylene chloride extract is washed with water, dried over sodium sulfate and evaporated to dryness. The residue is recrystallized from isopropanol and 41.5 g. of p-chloro-N-(2-morpholinoethyl)-benzamide, melting point 137° C., are obtained.

Workup

  1. customsubsequently evaporated to dryness
  2. customThen, the residue is evaporated twice more with 200 ml
  3. customThe phases are separated
  4. extractionthe methylene chloride extract
  5. washis washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness
  8. customThe residue is recrystallized from isopropanol and 41.5 g

Sources & evidence

ORD record
ord-ba2a56f0621d4c278a6a3d1dfb4ca5aa
Source dataset
uspto-grants-1980_07
Patent number
US04210754

Reaction notes

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