4-(Aminosulfonyl)-5-chlorophthalimide → 1-Pentanol

HRID 2412936Notes

Reaction equation

HRID 2412936 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[NH:8][C:6](=[O:7])[C:5]2=[CH:11][C:12]=1S(=O)(=O)N.NC1CCN(CC2C=CC=C(C(F)(F)F)C=2)CC1>>[CH2:6]([OH:7])[CH2:5][CH2:4][CH2:3][CH3:2].[O:7]=[C:6]1[C:5]2[C:4](=[CH:3][CH:2]=[CH:12][CH:11]=2)[C:9](=[O:10])[NH:8]1

Participants

4

Reactant 2

HCID 197334-(Aminosulfonyl)-5-chlorophthalimideHCID 128889291-{[3-(Trifluoromethyl)phenyl]methyl}piperidin-4-amine

Product 2

HCID 62761-PentanolHCID 6809Phthalimide

Procedure

Reaction of 4-chloro-5-sulfamoylphthalimide (10.1 g., 0.0386 mole) and 4-amino-1-(3-trifluoromethylbenzyl)piperidine (10.0 g., 0.0386 mole) in 200 ml. of n-pentanol according to the procedure of Example 1(a) afforded the crude 1,3-dioxoisoindole product purified by chromatography to yield 8.1 g. (42% yield) of 6-chloro-2,3-dihydro-1,3-dioxo-2-[1-[[3-(trifluoromethyl)phenyl]methyl]-4-piperidinyl]-1H-isoindole-5-sulfonamide. The NMR spectral data was consistent for the compound used without further purification below.

Sources & evidence

ORD record
ord-89c50013a4d74408a6bae3ee3d6af5fe
Source dataset
uspto-grants-1985_01
Patent number
US04495194

Reaction notes

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