Sodium Hydroxide → Mosapride

HRID 1608199Notes

Reaction equation

HRID 1608199 reaction equation
C([NH:4][C:5]1[C:28]([Cl:29])=[CH:27][C:8]([C:9]([NH:11][CH2:12][CH:13]2[O:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:14]2)=[O:10])=[C:7]([O:30][CH2:31][CH3:32])[CH:6]=1)(=O)C.[OH-].[Na+]>Cl>[NH2:4][C:5]1[C:28]([Cl:29])=[CH:27][C:8]([C:9]([NH:11][CH2:12][CH:13]2[O:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)[CH2:14]2)=[O:10])=[C:7]([O:30][CH2:31][CH3:32])[CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14877443HCID 14877443, compound

Product 1

HCID 119584MosaprideYield 77%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 4-acetylamino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]methyl]benzamide (2.0 g) and 10% hydrochloric acid (40 ml) is refluxed with stirring for 1 hour and cooled. The reaction mixture is neutralized with aqueous sodium hydroxide solution and extracted with chloroform. The organic layer is dried over magnesium sulfate and evaporated. The residue is recrystallized from ethanol to give the title compound (1.4 g), mp 151°-153° C.

Workup

  1. temperatureis refluxed
  2. temperaturecooled
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. customevaporated
  6. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-53c83969a61f4876ae96f05dd99d23ee
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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