4-(Aminosulfonyl)-5-chlorophthalimide → 2-[1-[(4-Bromophenyl)methyl]-4-piperidinyl]-6-chloro-2,3-dihydro-1,3-dioxo-1H-isoindole-5-sulfonamide

HRID 745833Notes

Reaction equation

HRID 745833 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]([Br:31])=[CH:27][CH:26]=2)[CH2:20][CH2:19]1>C(O)CCCC>[Br:31][C:28]1[CH:27]=[CH:26][C:25]([CH2:24][N:21]2[CH2:22][CH2:23][CH:18]([N:8]3[C:6](=[O:7])[C:5]4[C:4](=[CH:3][C:2]([Cl:1])=[C:12]([S:13]([NH2:14])(=[O:16])=[O:15])[CH:11]=4)[C:9]3=[O:10])[CH2:19][CH2:20]2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 197334-(Aminosulfonyl)-5-chlorophthalimideHCID 233124561-[(4-Bromophenyl)methyl]piperidin-4-amine

Product 1

HCID 133706032-[1-[(4-Bromophenyl)methyl]-4-piperidinyl]-6-chloro-2,3-dihydro-1,3-dioxo-1H-isoindole-5-sulfonamide

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

Reaction of a mixture of 4-chloro-5-sulfamoylphthalimide (6.48 g., 0.025 mole) and 4-amino-1-(4-bromobenzyl)piperidine (6.7 g., 0.025 mole) in n-pentanol according to the procedure of Example 1(a) afforded the 1,3-dioxoisoindole product. Purification of the crude product by triturating with n-heptane and crystallization from DMF-methanol afforded 6.9 g. (54%) of 2-[1-[(4-bromophenyl)methyl]-4-piperidinyl]-6-chloro-2,3-dihydro-1,3-dioxo-1H-isoindole-5-sulfonamide, m.p. 246°-247° (dec.).

Sources & evidence

ORD record
ord-4e3d973ab3094fd1b69a9e76759707aa
Source dataset
uspto-grants-1986_07
Patent number
US04600758

Reaction notes

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