Sodium Hydroxide → Doxazosin

HRID 428360

Reaktionsgleichung

Reaktionsgleichung von HRID 428360
[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C:9]([NH2:31])=[N:10][C:11]([N:13]3[CH2:18][CH2:17][N:16]([C:19]([CH:21]4[O:30][C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[O:23][CH2:22]4)=[O:20])[CH2:15][CH2:14]3)=[N:12][C:6]2=[CH:5][C:4]=1[O:32][CH3:33].Cl.[OH-].[Na+]>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C:9]([NH2:31])=[N:10][C:11]([N:13]3[CH2:14][CH2:15][N:16]([C:19]([CH:21]4[O:30][C:29]5[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=5[O:23][CH2:22]4)=[O:20])[CH2:17][CH2:18]3)=[N:12][C:6]2=[CH:5][C:4]=1[O:32][CH3:33]

Komponenten

3

Edukt 2

HCID 14798Sodium HydroxideHCID 11591230Doxazosin Monohydrochloride

Produkt 1

HCID 3157Doxazosin

Versuchsvorschrift

4-Amino-2-chloro-6,7-bismethoxyquinazoline (III) (3.2 grams, 13.35 mmole), Compound 4 from Example 2 (3.4 grains, 13.75 mmole) and n-butanol (72 ml) were subjected to a 50 ml round-bottom flask and heated under refluxing for 3.5 hours under a nitrogen atmosphere. Cooling to 75° C., the solid products were filtered and collected, dried in an oven to obtain 5.25 grams of Doxazosin hydrochloride (10.76 mmole, Yield: 81%). The Doxazosin hydrochloride was added to a 1N NaOH solution and heated for dissolution. After cooling, the solution was extracted with 150 ml of dichloromethane twice. The organic layer was filtered and dried with anhydrous sulfate, and concentrated to obtain 4.61 grams of white Doxazosin solid: 1H NMR (CDCl3) δ 3.63-4.09 (m, 8 H), 3.91 (s, 3H), 3.96 (s, 3H), 4.35 (dd, J=11.9, 7.9 Hz, 1H), 4.52 (dd, J=11.9, 2.4 Hz, 1H), 4.88 (dd, J=7.9, 2.4 Hz, 1H), 6.85-6.95 (m, 5H)

Aufarbeitung

  1. temperatureheated for dissolution
  2. temperatureAfter cooling
  3. extractionthe solution was extracted with 150 ml of dichloromethane twice
  4. filtrationThe organic layer was filtered
  5. dry with materialdried with anhydrous sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-69da2c6d5cec485f9abdf4cf929fe71a
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313293B1

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