4-Methoxystyrene → Trans-6-[2-(4-methoxyphenyl)ethenyl]-2-(3-piperidinopropyl)phthalazin-1(2H)-one hydrobromide

HRID 622125

Reaktionsgleichung

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[N:6]=[CH:5]2.Cl.ClCCCN1CCCCC1.Cl.C(N(C(C)C)CCCl)(C)C.[CH3:44][O:45][C:46]1[CH:53]=[CH:52][C:49]([CH:50]=[CH2:51])=[CH:48][CH:47]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(O)(C)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C.CS(C)=O>[BrH:1].[CH3:44][O:45][C:46]1[CH:53]=[CH:52][C:49](/[CH:50]=[CH:51]/[C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[N:7]([CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[N:6]=[CH:5]3)=[CH:48][CH:47]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

6-Bromo-2-(3-piperidinopropyl)phthalazin-1(2H)-one (7.2 gm, 0.018 mole) (prepared as in Example I, except that 1-(3-chloropropyl)piperidine hydrochloride was substituted for the 2-(diisopropylamino)ethyl chloride hydrochloride) was stirred into 10 ml DMSO plus 10 ml acetonitrile. To the resulting mixture was added 2.8 gm 4-methoxystyrene (0.021 mole), 0.1 gm tri(o-tolyl)phosphine, and 0.02 gm palladium acetate. The reaction mixture was stirred at reflux (95°-100° C.) for 24 hours. Allowed to cool to about 60° C. and diluted with 40 ml of isopropanol. Stirred for an hour, filtered, washed to colorless washings with isopropanol and dried. The product weighed 8.6 gm. After recrystallization from 50 ml methoxyethanol the product weighed 6.4 gm and melted at 248°-250° C.

Aufarbeitung

temperatureat reflux (95°-100° C.) for 24 hours
stirringStirred for an hour
filtrationfiltered
washwashed
washwashings with isopropanol
customdried
customAfter recrystallization from 50 ml methoxyethanol the product

Quellen und Nachweise

ORD-Eintrag: ord-92b25b7f9dfd4d2bb4eea1a7d0574cb1
Quelldatensatz: uspto-grants-1988_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04769369

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