Diisopropylethylamine → N-[4-{4-(1,2-benzisothiazol-3-yl)-1-piperazinyl}butyl]phthalimide

HRID 1073296Notes

Reaction equation

HRID 1073296 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:2]1.Br[CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31].C(N(CC)C(C)C)(C)C>CN(C=O)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:11][CH2:12][N:13]([CH2:17][CH2:18][CH2:19][CH2:20][N:21]3[C:25](=[O:26])[C:24]4[C:23](=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:22]3=[O:31])[CH2:14][CH2:15]2)=[N:2]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 93575N-(4-Bromobutyl)phthalimideHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazole

Product 1

HCID 10093606N-[4-{4-(1,2-benzisothiazol-3-yl)-1-piperazinyl}butyl]phthalimideYield 65.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

An 18.01 g sample of 1-(1,2-benzisothiazol-3-yl)piperazine (83.7 mmol), 29.5 g of N-(4-bromobutyl)phthalimide (104.6 mmol) and 36 mL of N,N-diisopropylethylamine (375.4 mmol) were added to 400 mL of dry DMF. The solution was heated at 80° C. for 18 hours, and the solvent was then removed in vacuo. The residue was dissolved in 500 mL of methylene chloride and was washed with saturated aqueous sodium bicarbonate. The combined aqueous layers were re-extracted with 2 portions of methylene chloride. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was crystallized from isopropanol with the addition of 4N HCl/isopropanol to give 23.03 g of the title compound as the hydrochloride, quarter hydrate, m.p. 253°-255° C.

Workup

  1. customthe solvent was then removed in vacuo
  2. dissolutionThe residue was dissolved in 500 mL of methylene chloride
  3. washwas washed with saturated aqueous sodium bicarbonate
  4. extractionThe combined aqueous layers were re-extracted with 2 portions of methylene chloride
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was crystallized from isopropanol with the addition of 4N HCl/isopropanol

Sources & evidence

ORD record
ord-9c86b90cb266441380ca85c84de9485e
Source dataset
uspto-grants-1990_11
Patent number
US04968792

Reaction notes

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