1-(2-Methoxyphenyl)piperazine → 2-(4-(4-(2-Methoxyphenyl)piperazin-1-yl)-3-hydroxybutyl)isoindoline-1,3-dione

HRID 404580Notes

Reaction equation

HRID 404580 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.ClC1C(Cl)=CC=CC=1N1CCN([CH2:29][CH:30]([OH:44])[CH2:31][CH2:32][N:33]2[C:41](=[O:42])[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34]2=[O:43])CC1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:29][CH:30]([OH:44])[CH2:31][CH2:32][N:33]2[C:41](=[O:42])[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34]2=[O:43])[CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 13461-(2-Methoxyphenyl)piperazineHCID 685058792-(4-(4-(2,3-Dichlorophenyl)-piperazin-1-yl)-3-hydroxybutyl)-isoindoline-1,3-dione

Product 1

HCID 685054142-(4-(4-(2-Methoxyphenyl)piperazin-1-yl)-3-hydroxybutyl)isoindoline-1,3-dioneYield 28%

Procedure

Prepared from 1-(2-methoxyphenyl)piperazine and 25 in a similar fashion as described above for 26a. Yield: 28%. Mp.: 192-194° C. 1H NMR (CDCl3): δ 1.79 (q, J 6.8, 2H), 2.41 (m, 2H), 2.61 (s, 2H), 2.85 (s, 2H), 3.07 (s, 4H), 3.77 (m, 1H), 3.85 (s, 3H), 3.91 (m, 2H), 6.86 (d, J 7.0, 1H), 6.91-6.95 (m, 2H), 7.00 (m, 1H), 7.85 (dd, J 5.5, 3.0, 2H), 7.71 (dd, J 5.4, 3.1, 2H). 13C NMR (CDCl3): δ 33.8, 35.4, 50.9, 53.6, 55.6, 64.1, 64.7, 111.3, 118.4, 121.2, 123.2, 123.4, 132.4, 134.1, 141.4, 152.4.

Sources & evidence

ORD record
ord-e431ea9930ed4c8e83794be8e36f94bc
Source dataset
uspto-grants-2014_06
Patent number
US08748608B2

Reaction notes

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