Methyl 4-chlorobenzoate → Moclobemide

HRID 2057457Notes

Reaction equation

HRID 2057457 reaction equation
CO[C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.[NH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>C(OCC)C>[Cl:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([NH:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[O:11])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 14307Methyl 4-chlorobenzoateHCID 4082852-Morpholinoethylamine

Product 1

HCID 4235Moclobemide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

8.2 G. of p-chlorobenzoic acid methyl ester and 6.25 g. of N-(2-aminoethyl)-morpholine are stirred together for 6 hours at 120° C. The mixture is then cooled to room temperature and 40 ml. of diethyl ether are added. Thereafter, the mixture is allowed to stand overnight in the refrigerator. The crystalline product is removed by filtration, washed with diethyl ether and recrystallized from isopropanol, and 2.6 g. of p-chloro-N-(2-morpholinoethyl)-benzamide are obtained, which is identical to the product obtained in Example 1.

Workup

  1. customThe crystalline product is removed by filtration
  2. washwashed with diethyl ether
  3. customrecrystallized from isopropanol, and 2.6 g

Sources & evidence

ORD record
ord-64dab14688a3471daa1066402a53421b
Source dataset
uspto-grants-1980_07
Patent number
US04210754

Reaction notes

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