Isopropanol → Terazosin

HRID 1067913Notes

Reaction equation

HRID 1067913 reaction equation
C(O)(C)C.[O:5]1[CH2:9][CH2:8][CH2:7][CH:6]1[C:10]([N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:11].[NH2:18][C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=2)[N:22]=[C:21](Cl)[N:20]=1>O>[CH3:30][O:29][C:26]1[CH:27]=[C:28]2[C:19]([NH2:18])=[N:20][C:21]([N:15]3[CH2:14][CH2:13][N:12]([C:10]([CH:6]4[O:5][CH2:9][CH2:8][CH2:7]4)=[O:11])[CH2:17][CH2:16]3)=[N:22][C:23]2=[CH:24][C:25]=1[O:31][CH3:32]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 27346411-(Tetrahydro-2-furoyl)piperazine

Product 1

HCID 5401TerazosinYield 108.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of iso-propanol (290 ml), water (50 ml) and N-(2-tetrahydrofuroyl)piperazine (20 g) were added, while stirring, 4-amino-2-chloro-6,7-dimethoxyquinazoline (22.2 g). The reaction mixture was heated to reflux and the reflux was maintained for about 35 hours. Then the reaction mixture was cooled to room temperature and stirred at this temperature for about 12 hours. The crystals were collected by filtration, washed with iso-propanol and dried in vacuo at 40° C. to yield 38.8 g (94%) of Terazosin.HCl dihydrate. See Trial K in Table I. Trial L was performed using a 5% percent volume of water.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperaturethe reflux was maintained for about 35 hours
  4. stirringstirred at this temperature for about 12 hours
  5. filtrationThe crystals were collected by filtration
  6. washwashed with iso-propanol
  7. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-b884f596763d41c59533e061ee197f02
Source dataset
uspto-grants-2001_06
Patent number
US06248888B1

Reaction notes

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