Terazosin Hydrochloride → Terazosin

HRID 2379400

Reaction equation

HRID 2379400 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C:9]([NH2:26])=[N:10][C:11]([N:13]3[CH2:18][CH2:17][N:16]([C:19]([CH:21]4[O:25][CH2:24][CH2:23][CH2:22]4)=[O:20])[CH2:15][CH2:14]3)=[N:12][C:6]2=[CH:5][C:4]=1[O:27][CH3:28].O.O.Cl>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C:9]([NH2:26])=[N:10][C:11]([N:13]3[CH2:18][CH2:17][N:16]([C:19]([CH:21]4[O:25][CH2:24][CH2:23][CH2:22]4)=[O:20])[CH2:15][CH2:14]3)=[N:12][C:6]2=[CH:5][C:4]=1[O:27][CH3:28]

Participants

3

Reactant 1

HCID 63016Terazosin Hydrochloride

Product 1

HCID 5401TerazosinYield 90.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a 500-mL round-bottom flask containing 5.19 g (0.011 mol) of terazosin monohydrochloride dihydrate was added 250 mL of dry acetone and several glass boiling beads. The flask was fitted with a Dean-Stark trap and reflux condensor. The heterogenous mixture was heated under reflux for five days. After cooling, the undissolved white solid remaining in the flask was collected by vacuum filtration to yield 4.3 g (0.010 mol, 90.9% yield) of the anhydrous crystalline polymorph of terazosin of this invention. The material was found by its powder x-ray diffraction pattern to be free of both the prior art anhydrous crystalline modification and the dihydrate form.

Workup

  1. customThe flask was fitted with a Dean-Stark trap
  2. temperaturereflux condensor
  3. temperatureThe heterogenous mixture was heated
  4. temperatureunder reflux for five days
  5. temperatureAfter cooling
  6. filtrationwas collected by vacuum filtration

Sources & evidence

ORD record
ord-c7aa683dcf7d443886995c02b7c0e72e
Source dataset
uspto-grants-1994_11
Patent number
US05362730

Linked notes

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