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

HRID 416487Notes

Reaction equation

HRID 416487 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH2:10])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[O:20]=[C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23](=[O:30])[N:22]1[CH2:31][CH2:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][S:33]([CH2:32][CH2:31][N:22]2[C:21](=[O:20])[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]2=[O:30])(=[O:34])=[O:35])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3087392-Phthalimidoethanesulfonyl chlorideHCID 31633331-(Propan-2-yl)piperidin-4-amine

Product 1

HCID 666250362-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid (1-isopropyl-piperidin-4-yl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.00 g (7.032 mmol) 1-Isopropyl-piperidin-4-ylamine (commercially available, or obtainable as described in EP 1479676) was dissolved in 100 ml dichloromethane. Subsequently 1.38 ml (1.1 equiv.) diisopropylethylamine (DIPEA) and 2.12 g (1.1 equiv.) 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonyl chloride (commercially available) were added. The resulting mixture was stirred for 5 h at room temperature. After complete conversion the mixture was diluted with 100 ml dichloromethane and washed with 150 ml water. The organic phase was then washed with 100 ml of a half saturated NaHCO3-solution and finally with brine. Drying over anhydrous MgSO4 and removal of the solvent by evaporation under reduced pressure gave crude 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid (1-isopropyl-piperidin-4-yl)-amide as a light yellow foam. Yield: 2.48 g MS (ES+): m/e=380.

Workup

  1. washwashed with 150 ml water
  2. washThe organic phase was then washed with 100 ml of a half saturated NaHCO3-solution and finally with brine
  3. dry with materialDrying over anhydrous MgSO4 and removal of the solvent by evaporation under reduced pressure

Sources & evidence

ORD record
ord-d50f3bdecd2c4678bc2f3790f3e0e5c1
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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