Ethanol → Mosapride

HRID 1608200Notes

Reaction equation

HRID 1608200 reaction equation
[Cl:1][C:2]1[C:3]([N+:29]([O-])=O)=[CH:4][C:5]([O:26][CH2:27][CH3:28])=[C:6]([CH:25]=1)[C:7]([NH:9][CH2:10][CH:11]1[O:16][CH2:15][CH2:14][N:13]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:12]1)=[O:8].C(O)C>C(OCC)(=O)C>[NH2:29][C:3]1[C:2]([Cl:1])=[CH:25][C:6]([C:7]([NH:9][CH2:10][CH:11]2[O:16][CH2:15][CH2:14][N:13]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)[CH2:12]2)=[O:8])=[C:5]([O:26][CH2:27][CH3:28])[CH:4]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 19848618HCID 19848618, compound

Product 1

HCID 119584MosaprideYield 53.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Stannous chloride dihydrate (5.4 g) is added to a stirred mixture of 5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]methyl]-4-nitrobenzamide (2.2 g), ethanol (30 ml), and ethyl acetate (30 ml). The reaction mixture is stirred at 70° C. for 2 hours and concentrated. The residue is basified with aqueous potassium carbonate solution and extracted with ethyl acetate. The organic layer is washed successively with water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and evaporated. The residue is recrystallized from ethanol to give the title compound (1.1 g), mp 151°-153° C.

Workup

  1. concentrationconcentrated
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is washed successively with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-3c416a7929d34c378919588d765a2cc9
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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