Doxazosin → Doxazosin Mesylate

HRID 1016364

Reaction equation

HRID 1016364 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:19]([NH2:20])=[N:18][C:17]([N:21]3[CH2:26][CH2:25][N:24]([C:27]([CH:29]4[O:38][C:37]5[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=5[O:31][CH2:30]4)=[O:28])[CH2:23][CH2:22]3)=[N:16][C:11]2=[CH:12][C:13]=1[O:14][CH3:15].CN1CCCC1=O>CO>[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:19]([NH2:20])=[N:18][C:17]([N:21]3[CH2:22][CH2:23][N:24]([C:27]([CH:29]4[O:38][C:37]5[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=5[O:31][CH2:30]4)=[O:28])[CH2:25][CH2:26]3)=[N:16][C:11]2=[CH:12][C:13]=1[O:14][CH3:15].[CH3:1][S:2]([OH:5])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 3157DoxazosinHCID 6395Methanesulfonic Acid2×HCID 13387N-methyl-2-pyrrolidone

Product 1

HCID 62978Doxazosin MesylateYield 136.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.1 g of anhydrous methanesulfonic acid were added to a stirred mixture of 27.1 g of doxazosin, 54 ml of N-methyl-2-pyrrolidone and 250 ml of methanol in a 500 ml three-necked round-bottomed flask. During this, the internal temperature rose to 30° C., and a solution formed. After the addition of the methanesulfonic acid was complete, the reaction mixture was filtered into a second 500 ml three-necked round-bottomed flask, and the filtrate was stirred for 5 h. After completion of the stirring time, the resulting precipitate was filtered off with suction and washed 2× with 50 ml of methanol each time. 45 g of moist doxazosin mesylate (modification D) were obtained. This corresponds to 28.5 g of dry substance and a yield of 86.7%.

Workup

  1. customrose to 30° C.
  2. customa solution formed
  3. filtrationthe reaction mixture was filtered into a second 500 ml three-necked round-bottomed flask
  4. filtrationAfter completion of the stirring time, the resulting precipitate was filtered off with suction
  5. washwashed 2× with 50 ml of methanol each time

Sources & evidence

ORD record
ord-142944fb95eb4375af8c99e73f2ec60e
Source dataset
uspto-grants-2002_11
Patent number
US06476033B1

Linked notes

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