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

HRID 434666Notes

Reaction equation

HRID 434666 reaction equation
[O:1]=[S:2]1(=[O:21])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])[N:3]1[C:12]([CH3:20])([CH2:16][CH2:17][CH2:18]O)[C:13]([NH2:15])=[O:14].O>C1(C)C(C)=CC=CC=1>[O:1]=[S:2]1(=[O:21])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])[N:3]1[C:12]1([CH3:20])[CH2:16][CH2:17][CH2:18][NH:15][C:13]1=[O:14]

Participants

4

Reactant 2

HCID 962WaterHCID 204918232-(2,3-Dihydro-1,1-dioxido-3-oxo-1,2-benzisothiazol-2-yl)-5-hydroxy-2-methyl-valeramid

Product 1

HCID 130410503-(2,3-Dihydro-1,1-dioxido-3-oxo-1,2-benzisothiazol-2-yl)-3-methyl-2-oxo-piperidineYield 37%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

5 g 2-(2,3-Dihydro-1,1-dioxido-3-oxo-1,2-benzisothiazol-2-yl)-5-hydroxy-2-methyl-valeramid are dissolved in 150 ml of xylene and the resulting solution is boiled under reflux for several hours, using a water separator. After the theoretical quantity of water has been separated off, the mixture is allowed to cool and concentrated in vacuo to a small volume. The precipitate is filtered off and recrystallized from n-butanol to give 3-(2,3-dihydro-1,1-dioxido-3-oxo-1,2-benzisothiazol-2-yl)-3-methyl-2-oxo-piperidine in the form of white crystals melting at 211° to 215° C., identical with the product obtained in example 1. The yield is 37% of the theoretical.

Workup

  1. temperatureunder reflux for several hours
  2. customAfter the theoretical quantity of water has been separated off
  3. temperatureto cool
  4. concentrationconcentrated in vacuo to a small volume
  5. filtrationThe precipitate is filtered off
  6. customrecrystallized from n-butanol

Sources & evidence

ORD record
ord-b411dac2d77045c284ce16a34c3c2bf1
Source dataset
uspto-grants-1983_08
Patent number
US04399145

Reaction notes

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