1-Pentanol → Phthalimide

HRID 745837Notes

Reaction equation

HRID 745837 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(OCC=C)=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 3

HCID 62761-PentanolHCID 197334-(Aminosulfonyl)-5-chlorophthalimideHCID 233124454-Amino-1-[4-(2-propenyloxy)benzyl]piperidine

Product 1

HCID 6809Phthalimide

Procedure

Reaction of 4-chloro-5-sulfamoylphthalimide (4.54 g., 0.0174 mole) and 4-amino-1-[4-(2-propenyloxy)benzyl]piperidine (4.29 g., 0.0174 mole) in 100 ml. of n-pentanol at reflux temperature for 24 hrs. according to the procedure of Example 1(a) afforded crude 1,3-dioxoisoindole product. Purification was carried out by treating with methanol-decolorizing charcoal followed by trituration with ether to afford 4.8 g. (57%) of the 1,3-dioxoisoindole used without further purification below.

Sources & evidence

ORD record
ord-93f67a613d834704a939bf4a90a003e9
Source dataset
uspto-grants-1986_07
Patent number
US04600758

Reaction notes

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