Isobutanol → Terazosin

HRID 1067912Notes

Reaction equation

HRID 1067912 reaction equation
C(O)C(C)C.[O:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[C:11]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:12].[NH2:19][C:20]1[C:29]2[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=2)[N:23]=[C:22](Cl)[N:21]=1>O>[CH3:31][O:30][C:27]1[CH:28]=[C:29]2[C:20]([NH2:19])=[N:21][C:22]([N:16]3[CH2:15][CH2:14][N:13]([C:11]([CH:7]4[O:6][CH2:10][CH2:9][CH2:8]4)=[O:12])[CH2:18][CH2:17]3)=[N:23][C:24]2=[CH:25][C:26]=1[O:32][CH3:33]

Participants

5

Reactant 3

HCID 6560IsobutanolHCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 27346411-(Tetrahydro-2-furoyl)piperazine

Product 1

HCID 5401TerazosinYield 109.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of iso-butanol (306 ml), water (34 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 13 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-butanol and dried in vacuo at 40° C. to yield 39.2 g (91.9%) of Terazosin.HCl dihydrate. See Trial A in Table I.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperaturethe reflux was maintained for about 13 hours
  4. stirringstirred at this temperature for about 12 hours
  5. filtrationThe crystals were collected by filtration
  6. washwashed with iso-butanol
  7. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-7137cfd568dc41b6bd12c698618ef1c2
Source dataset
uspto-grants-2001_06
Patent number
US06248888B1

Reaction notes

Loading…