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

HRID 2412934Notes

Reaction equation

HRID 2412934 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(OC)=CC=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 126418411-(4-Methoxybenzyl)piperidin-4-amine

Product 2

HCID 62761-PentanolHCID 6809Phthalimide

Procedure

Reaction of 4-chloro-5-sulfamoylphthalimide (5.21 g., 0.02 mole) and 4-amino-1-(4-methoxybenzyl)piperidine (4.5 g., 0.02 mole) in 80 ml. of n-pentanol according to the procedure of Example 1(a) afforded the crude 1,3-dioxoisoindole product purified by chromatography (silica gel, ethyl acetate-n-hexane) to yield 2.88 g. (31%) of 6-chloro-2,3-dihydro-2-[1-[(4-methoxyphenyl)methyl]-4-piperidinyl]-1,3-dioxo-1H-isoindole-5-sulfonamide. The NMR spectral data was consistent for the compound used without further purification below.

Sources & evidence

ORD record
ord-f94800382d7843ffa9b7c6c3d5e9ec2e
Source dataset
uspto-grants-1985_01
Patent number
US04495194

Reaction notes

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