Phthalimide potassium salt → (Z)-2-(4-Chlorobut-2-en-1-yl)isoindoline-1,3-dione
Reaction equation
[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]Participants
3
Procedure
Cis-4-[4-(5-chloro-2-methylphenyl)piperazinyl]-2-buten-1-amine: according to the method of Example 5, phthalimide potassium salt was reacted with cis-1,4-dihydro-2-butene to obtain N-(cis-4-chloro-2-buten-1-yl)phthalimide; which was then reacted with 5-chloro-2-methylphenylpiperazine to obtain N-{4-[4-(5-chloro-2-methylphenyl)piperazinyl]-cis-2-buten-1-yl}phthalimide, which was then reacted with hydrazine hydrate. Yield: 85.7%. Hydrochloride mp: 127-129° C. 1HNMR (ppm, CDCl3) δ: 1.56 (br-s, 4H), 2.23 (s, 3H), 2.71 (br-s, 2H, NH2), 2.96 (m, 4H), 3.12 (d, J=7.0 Hz), 3.41 (d, J=6.72 Hz, 2H), 5.60 (m, 1H), 5.73 (m, 1H), 6.96 (m, 2H), 7.08 (d, J=7.84, 1H).
Sources & evidence
- ORD record
- ord-4526b6e5272a43178597e9f898d24b20
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08829001B2
Reaction notes
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