Doxazosin → Doxazosin Mesylate

HRID 1969340

Reaction equation

HRID 1969340 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14]([NH2:15])=[N:13][C:12]([N:16]3[CH2:21][CH2:20][N:19]([C:22]([CH:24]4[O:33][C:32]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[O:26][CH2:25]4)=[O:23])[CH2:18][CH2:17]3)=[N:11][C:6]2=[CH:7][C:8]=1[O:9][CH3:10].[CH3:34][S:35]([OH:38])(=[O:37])=[O:36]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14]([NH2:15])=[N:13][C:12]([N:16]3[CH2:17][CH2:18][N:19]([C:22]([CH:24]4[O:33][C:32]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[O:26][CH2:25]4)=[O:23])[CH2:20][CH2:21]3)=[N:11][C:6]2=[CH:7][C:8]=1[O:9][CH3:10].[CH3:34][S:35]([OH:38])(=[O:37])=[O:36]

Participants

4

Reactant 2

HCID 3157DoxazosinHCID 6395Methanesulfonic Acid

Product 1

HCID 62978Doxazosin MesylateYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

Doxazosin base (0.277 mol; 125 g) was charged in acetone (1875 ml) and stirred at 25° C. to obtain slurry. On cooling the slurry to 10-15° C., methanesulphonic acid (0.33 mol; 31.96 g) was added to it. The contents were stirred for 10-15 min at 10-15° C. and then stirring continued at 25° C. for 2 hr. The solid obtained was filtered, washed with acetone and dried at 50-55° C. to obtain solid. The solid was purified by refluxing in methanol (1500 ml) for 1 hr. The slurry was cooled to room temperature, filtered, washed with methanol and then dried at 60° C. under reduced pressure to obtain 135 g of pure doxazosin mesylate (HPLC purity −99.81%).

Workup

  1. customto obtain slurry
  2. temperatureOn cooling the slurry to 10-15° C.
  3. stirringThe contents were stirred for 10-15 min at 10-15° C.
  4. stirringstirring
  5. customThe solid obtained
  6. filtrationwas filtered
  7. washwashed with acetone
  8. customdried at 50-55° C.
  9. customto obtain solid
  10. customThe solid was purified
  11. temperatureby refluxing in methanol (1500 ml) for 1 hr
  12. temperatureThe slurry was cooled to room temperature
  13. filtrationfiltered
  14. washwashed with methanol
  15. customdried at 60° C. under reduced pressure

Sources & evidence

ORD record
ord-9ce08473a972475283b8c15229ce2a66
Source dataset
uspto-grants-2013_04
Patent number
US08426590B2

Linked notes

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