2-Phthalimidoethanesulfonyl chloride → 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid (1-isopropyl-piperidin-4-yl)-methyl-amide

HRID 416495Notes

Reaction equation

HRID 416495 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][CH3:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[O:12]=[C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[N:14]1[CH2:23][CH2:24][S:25](Cl)(=[O:27])=[O:26]>>[CH:1]([N:4]1[CH2:5][CH2:6][CH:7]([N:10]([CH3:11])[S:25]([CH2:24][CH2:23][N:14]2[C:13](=[O:12])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:22])(=[O:26])=[O:27])[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 3087392-Phthalimidoethanesulfonyl chlorideHCID 3159676N-methyl-1-(propan-2-yl)piperidin-4-amine

Product 1

HCID 666243422-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid (1-isopropyl-piperidin-4-yl)-methyl-amide

Procedure

2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid (1-isopropyl-piperidin-4-yl)-methyl-amide was prepared by an analogous procedure as described for example 1 i) starting from 171.3 mg (1.1 mmol) (1-isopropyl-piperidin-4-yl)-methyl-amine and 300 mg (1 equiv.) 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonyl chloride. 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid (1-isopropyl-piperidin-4-yl)-methyl-amide was obtained as a light yellow foam. Yield: 385 mg MS (ES+): m/e=394.

Workup

  1. custom2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid (1-isopropyl-piperidin-4-yl)-methyl-amide was prepared by an analogous procedure

Sources & evidence

ORD record
ord-aab168e1378e43c2a419f874ff73e027
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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