Phthalimide potassium salt → 2-((2E)-4-chlorobut-2-en-1-yl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 72634

Reaktionsgleichung

Reaktionsgleichung von HRID 72634
[Cl:1][C:2]1C=C[C:5](C)=[C:6](N2CCN(C/C=C/CN)CC2)[CH:7]=1.[K].[C:21]1(=[O:31])[NH:25][C:24](=[O:26])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]12>>[Cl:1][CH2:2]/[CH:7]=[CH:6]/[CH2:5][N:25]1[C:21](=[O:31])[C:22]2=[CH:30][CH:29]=[CH:28][CH:27]=[C:23]2[C:24]1=[O:26]

Komponenten

3

Edukt 2

HCID 24194345Phthalimide potassium saltHCID 67361178Trans-4-[4-(5-chloro-2-methylphenyl)piperazinyl]-2-buten-1-amine

Produkt 1

HCID 57093742-((2E)-4-chlorobut-2-en-1-yl)-2,3-dihydro-1H-isoindole-1,3-dione

Versuchsvorschrift

Trans-4-[4-(5-chloro-2-methylphenyl)piperazinyl]-2-buten-1-amine: according to the method of Example 1, phthalimide potassium salt was reacted with trans-1,4-dihydro-2-butene to obtain N-(trans-4-chloro-2-buten-1-yl)phthalimide, mp: 108-110° C.; which was then reacted with 5-chloro-2-methylphenylpiperazine to obtain N-{4-[4-(5-chloro-2-methylphenyl)piperazinyl]-trans-2-buten-1-yl}phthalimide, which was then reacted with hydrazine hydrate to obtain the product. Yield: 89.3%. Hydrochloride mp: 140-142° C. 1HNMR (ppm, CDCl3) δ: 1.46 (br-s, 4H), 2.25 (s, 3H), 2.61 (br-s, 2H, NH2), 2.93 (m, 4H), 3.10 (d, J=7.0 Hz), 3.39 (d, J=6.72 Hz, 2H), 5.58 (m, 1H), 5.71 (m, 1H), 6.96 (m, 2H), 7.06 (d, J=7.84, 1H).

Quellen und Nachweise

ORD-Eintrag
ord-35a96b6368d6438a874d7ac665bacceb
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829001B2

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