4-(Aminosulfonyl)-5-chlorophthalimide → Phthalimide

HRID 2412933Notes

Reaction equation

HRID 2412933 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(Br)=CC=2)CC1>C(O)CCCC>[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 233124561-[(4-Bromophenyl)methyl]piperidin-4-amine

Product 1

HCID 6809Phthalimide

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-15eb8271cd874bb29c04b6f3182e6e5a
Source dataset
uspto-grants-1985_01
Patent number
US04495194

Reaction notes

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