Water → 3-(2,3-Dihydro-1,1-dioxido-3-oxo-1,2-benzisothiazol-2-yl)-3-methyl-2-oxo-piperidine

HRID 434664Notes

Reaction equation

HRID 434664 reaction equation
Br[C:2]1([CH3:9])[CH2:7][CH2:6][CH2:5][NH:4][C:3]1=[O:8].[Na].[O:11]=[C:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[S:14](=[O:22])(=[O:21])[NH:13]1.O>CN(C)C=O>[O:21]=[S:14]1(=[O:22])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:12](=[O:11])[N:13]1[C:2]1([CH3:9])[CH2:7][CH2:6][CH2:5][NH:4][C:3]1=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 5143SaccharinHCID 5360545SodiumHCID 130410493-Bromo-3-methylpiperidin-2-one

Product 1

HCID 130410503-(2,3-Dihydro-1,1-dioxido-3-oxo-1,2-benzisothiazol-2-yl)-3-methyl-2-oxo-piperidineYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.8 g of 3-bromo-3-methyl-2-piperidone and 8 g of the dried sodium salt of 2,3-dihydro-3-oxo-1,2-benzisothiazol-1,1-dioxide are heated while stirring to 110°-115° in 25 ml of distilled dimethyl formamide for a period of 75 minutes. After cooling 75 ml of water are added and the stirring is continued for further 30 minutes. The precipitate is filtered off, washed with water, dried in a vacuum at 80° C. and then recrystallized from n-butanol. 3-(2,3-Dihydro-1,1-dioxido-3-oxo-1,2-benzisothiazol-2-yl)-3-methyl-2-oxo-piperidine melting at 211° to 215° C. is thus obtained in a yield of 24% of the theoretical.

Workup

  1. additionare added
  2. filtrationThe precipitate is filtered off
  3. washwashed with water
  4. customdried in a vacuum at 80° C.
  5. customrecrystallized from n-butanol

Sources & evidence

ORD record
ord-5d6730bb6236456fbffeeb8de2a2ad24
Source dataset
uspto-grants-1983_08
Patent number
US04399145

Reaction notes

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