Potassium Carbonate → 2-(4-(4-(2,3-Dimethylphenyl)piperazin-1-yl)-3-hydroxybutyl)isoindoline-1,3-dione

HRID 1626308Notes

Reaction equation

[O:1]1[CH2:3][CH:2]1[CH2:4][CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16].C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:24][C:25]1[C:30]([CH3:31])=[CH:29][CH:28]=[CH:27][C:26]=1[N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>CN(C)C=O>[CH3:24][C:25]1[C:30]([CH3:31])=[CH:29][CH:28]=[CH:27][C:26]=1[N:32]1[CH2:33][CH2:34][N:35]([CH2:3][CH:2]([OH:1])[CH2:4][CH2:5][N:6]2[C:14](=[O:15])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]2=[O:16])[CH2:36][CH2:37]1

Participants

Conditions

Temperature: 110 °C

Procedure

To a mixture of 2-(2-(oxiran-2-yl)ethyl)isoindoline-1,3-dione obtained in step 2 (0.30 g, 1.38 mmol) and potassium carbonate (0.48 g, 3.45 mmol) in N,N-dimethylformamide (3.0 ml), was added 1-(2,3-dimethylphenyl)piperazine hydrochloride (0.31 g, 1.38 mmol) at room temperature. The resulting reaction mixture was stirred at 110° C. for 18 hours. After the reaction complete, the reaction mixture thus obtained was filtered through a plug of Celite. The filtrate was concentrated under reduced pressure to obtain the title compound (0.26 g). The compound was used for the next step without further purification.

Workup

customThe resulting reaction mixture
customAfter the reaction complete, the reaction mixture thus obtained
filtrationwas filtered through a plug of Celite
concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-efd2fed5268e435e9d7457c3c1ed6d7f
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785453B2

Reaction notes

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