4-Chlorobenzoic Acid → Moclobemide

HRID 2057460Notes

Reaction equation

HRID 2057460 reaction equation
P(Cl)(Cl)Cl.[NH2:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[Cl:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=1>N1C=CC=CC=1>[Cl:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH:5][CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[O:20])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 63184-Chlorobenzoic AcidHCID 24387Phosphorus trichlorideHCID 4082852-Morpholinoethylamine

Product 1

HCID 4235Moclobemide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
90 °C

Procedure

2.8 G. of phosphorus trichloride in 20 ml. of pyridine are added to 5.2 g. of N-(2-aminoethyl)-morpholine in 80 ml. of pyridine at -5° C. over a period of 15 minutes, with stirring. The mixture is stirred for 30 minutes at -5° C. and 90 minutes at room temperature. Then, 3.1 g. of p-chlorobenzoic acid are added and the mixture is heated for 3 hours at 90° C. This mixture is evaporated to dryness and the residue is evaporated twice more with 100 ml. of toluene each time. The solid residue is taken up in 100 ml. of methylene chloride and 100 ml. of ice-water and the mixture is 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. The residue is recrystallized from isopropanol and 1.3 g. of p-chloro-N-(2-morpholinoethyl)-benzamide are obtained, which is identical to the product obtained in Example 1.

Workup

  1. stirringThe mixture is stirred for 30 minutes at -5° C. and 90 minutes at room temperature
  2. customThis mixture is evaporated to dryness
  3. customthe residue is evaporated twice more with 100 ml
  4. customThe phases are separated
  5. extractionthe methylene chloride extract
  6. washis washed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe residue is recrystallized from isopropanol and 1.3 g

Sources & evidence

ORD record
ord-8c71e2759af64fad85a8cae58e8c33cd
Source dataset
uspto-grants-1980_07
Patent number
US04210754

Reaction notes

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