Terazosin Hydrochloride → Terazosin

HRID 2379399Notes

Reaction equation

HRID 2379399 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>C(O)C>[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 5401Terazosin

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 2-liter round-bottom flask containing 71.0 g (0.15 mol) of terazosin monohydrochloride dihydrate was added 1300 mL of absolute ethanol, a stirring bar 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 two days. After cooling, the undissolved white solid remaining in the flask was collected by vacuum filtration and washed with dry acetone to yield 60.9 g (0.143 mol, 93.5%) 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 two days
  5. temperatureAfter cooling
  6. filtrationwas collected by vacuum filtration
  7. washwashed with dry acetone

Sources & evidence

ORD record
ord-c6467a64a2334146a6dbff801f20d4a7
Source dataset
uspto-grants-1994_11
Patent number
US05362730

Reaction notes

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