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

HRID 745835Notes

Reaction equation

HRID 745835 reaction equation
[Cl:1][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]=1[S:13](=[O:16])(=[O:15])[NH2:14].N[CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[CH2:20][CH2:19]1>>[CH2:6]([OH:7])[CH2:5][CH2:4][CH2:3][CH3:2].[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:6](=[O:7])[N:8]([CH:18]3[CH2:23][CH2:22][N:21]([CH2:24][C:25]4[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=4)[CH2:20][CH2:19]3)[C:9]2=[O:10])=[CH:11][C:12]=1[S:13]([NH2:14])(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 197334-(Aminosulfonyl)-5-chlorophthalimideHCID 126418411-(4-Methoxybenzyl)piperidin-4-amine

Product 2

HCID 62761-PentanolHCID 233124496-Chloro-2,3-dihydro-2-[1-[(4-methoxyphenyl)methyl]-4-piperidinyl]-1,3-dioxo-1H-isoindole-5-sulfonamide

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-811d287b556843758a248cc3e7519b32
Source dataset
uspto-grants-1986_07
Patent number
US04600758

Reaction notes

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