I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.
Phthalimide is a reagent used to transform allyl- and alkyl halides into protected primary amines. . It is used as a precursor to other organic compounds as a masked source of ammonia.
John C. Sheehan.; William A. Bolhofer. An Improved Procedure for the Condensation of Potassium Phthalimide with Organic Halides. J. Am. Chem. Soc. 1950, 72 (2), 2786-2788.
Lı?dia M Lima.; Paulo Castro.; Alexandre L Machado.; Carlos Alberto M Fraga.; Claire Lugnier.; Vera Lúcia Gonçalves de Moraes.; Eliezer J Barreiro. Synthesis and anti-inflammatory activity of phthalimide derivatives, designed as new thalidomide analogues. Bioorg. Med. Chem.. 2002, 10 (9),3067-3073.
For use in the Gabriel synthesis of primary amines, see: Potassium phthalimide, A11134. For an example of N-alkylation in the presence of K2CO3, see: Org. Synth. Coll., 2, 83 (1943). The N-alkylation by alkyl halides can be effected using KF, RbF or CsF as base; NaF and LiF are ineffective: J. Am. Chem. Soc., 99, 498 (1977).
The direct conversion of alcohols to N-alkylphthalimides and hence to amines can be effected in the presence of the Mitsunobu reagent: Org. Synth. Coll., 7, 501 (1990):