Allyl chloride → N-Allylphthalimide

HRID 1774262Notes

Reaction equation

HRID 1774262 reaction equation
[K].[C:2]1(=[O:12])[NH:6][C:5](=[O:7])[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]12.[CH2:13](Cl)[CH:14]=[CH2:15]>CN(C=O)C>[CH2:15]([N:6]1[C:2](=[O:12])[C:3]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:4]2[C:5]1=[O:7])[CH:14]=[CH2:13]

Participants

4

Reactant 2

HCID 7850Allyl chlorideHCID 24194345Phthalimide potassium salt

Product 1

HCID 224401N-Allylphthalimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phthalimide potassium salt can be alkylated with allyl chloride in DMF to produce N-allylphthalimide. Under the Heck reaction conditions (Patel et al. 1977), N-allylphthalimide reacted with aryl bromide to give N-cinnamyl phthalimide. Upon treatment with hydrazine, cinnamyl amine was obtained from N-cinnamyl phthalimide (FIG. 28).

Sources & evidence

ORD record
ord-e64065010a6a44099b842d7b42928431
Source dataset
uspto-grants-2016_02
Patent number
US09260382B2

Reaction notes

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