Water → HCID 10645029, compound

HRID 339737Notes

Reaction equation

HRID 339737 reaction equation
[N:1]1([C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[S:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:17][CH2:18][CH2:19][N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[S:9]1[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:7]([N:1]2[CH2:6][CH2:5][N:4]([CH2:17][CH2:18][CH2:19][N:20]3[C:24](=[O:25])[C:23]4[C:22](=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:21]3=[O:30])[CH2:3][CH2:2]2)=[N:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazole

Product 1

HCID 10645029HCID 10645029, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(piperazin-1-yl)benzo[d]isothiazole (1.75 g, 8.0 mmol), N-(3-bromopropyl)-phthalimide (1.96 mmol, 7.3 mmol) and K2CO3 (2.21 g, 16.0 mol) in DMF (10 mL) was stirred at 80° C. for 3 hours. The reaction mixture was poured into water (100 mL) and extracted with ethyl acetate (150 mL). The organic phase was dried over MgSO4 and evaporated under vacuum. The residue was further purified by flash column chromatography to provide 2-(3-(4-(benzo[d]isothiazol-3-yl)piperazin-1-yl)propyl)isoindoline-1,3-dione as an intermediate (1.49 g, 3.67 mmol, 50%).

Workup

  1. extractionextracted with ethyl acetate (150 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. customevaporated under vacuum
  4. customThe residue was further purified by flash column chromatography

Sources & evidence

ORD record
ord-f168c44ec4e34e1c939de76796d3d514
Source dataset
uspto-grants-2014_11
Patent number
US08895558B2

Reaction notes

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