4-Chlorobenzoic Acid → Moclobemide

HRID 2057456Notes

Reaction equation

HRID 2057456 reaction equation
C(OC(Cl)=O)C.[Cl:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1.C(N(CC)CC)C.[NH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>CC(C)=O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([NH:24][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[O:14])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 63184-Chlorobenzoic AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4082852-Morpholinoethylamine

Product 1

HCID 4235Moclobemide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

5.3 Ml. of chloroformic acid ethyl ester are added dropwise to a solution of 8.6 g. of p-chlorobenzoic acid and 7.6 ml. of triethylamine in 150 ml. of acetone, with stirring and cooling with ice-water. After one hour at 0° C., a solution of 6.5 g. of N-(2-aminoethyl)-morpholine in 50 ml. of acetone is added dropwise to the mixture and the mixture is then stirred overnight at room temperature. Thereafter it is concentrated, allowed to stand for 2 hours in the refrigerator and filtered. The filtrate is evaporated to dryness and the residue is taken up in 250 ml. of water and 250 ml. of methylene chloride. The phases are separated and the methylene chloride extract is dried over sodium sulfate and evaporated. The residue is recrystallized from isopropanol and 7.8 g. of p-chloro-N-(2-morpholinoethyl)-benzamide are obtained, which is identical to the product obtained in Example 1.

Workup

  1. concentrationThereafter it is concentrated
  2. waitto stand for 2 hours in the refrigerator
  3. filtrationfiltered
  4. customThe filtrate is evaporated to dryness
  5. customThe phases are separated
  6. extractionthe methylene chloride extract
  7. dry with materialis dried over sodium sulfate
  8. customevaporated
  9. customThe residue is recrystallized from isopropanol and 7.8 g

Sources & evidence

ORD record
ord-d2c76ec1e1a7474f966118c63ec9ddcb
Source dataset
uspto-grants-1980_07
Patent number
US04210754

Reaction notes

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