Hydrochloric Acid → Midodrine hydrochloride

HRID 1278960Notes

Reaction equation

HRID 1278960 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:17][CH3:18])=[C:7]([CH:9]([OH:16])[CH2:10][NH:11][C:12]([CH2:14][NH2:15])=[O:13])[CH:8]=1.C(O)C.[ClH:22]>C(O)(C)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:17][CH3:18])=[C:7]([CH:9]([OH:16])[CH2:10][NH:11][C:12]([CH2:14][NH2:15])=[O:13])[CH:8]=1.[ClH:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4195Midodrine

Product 1

HCID 18340Midodrine hydrochlorideYield 96%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The reaction vessel is charged with 5.0 g Midodrine base and 60 ml ethanol. The mixture is heated to reflux to obtain a clear solution. To the hot mixture is added 6.3 ml of a 22% solution of hydrochloric acid in isopropanol in portions. During the addition, the Midodrine HCl will crystallize from solution. After cooling to 5°-10° C., the product is filtered to afford 4.8 g (96% yield) of Midodrine HCl (m.p.: 200.8°-201.8° C.).

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. customto obtain a clear solution
  4. additionDuring the addition
  5. customthe Midodrine HCl will crystallize from solution
  6. temperatureAfter cooling to 5°-10° C.
  7. filtrationthe product is filtered

Sources & evidence

ORD record
ord-4c6a70e6997b460b88b6b7e404487cec
Source dataset
uspto-grants-2002_09
Patent number
US06444851B1

Reaction notes

Loading…