Phthalimide → HCID 19744579, compound

Participants

Reaction Steps

As an alternative method of synthesizing the above compound, phthalimide and 1-bromo-6,6-dimethyl-2-hepten-4-yne (a mixture of E and Z forms in a ratio of about 3:1) are reacted in dimethylformamide. The resulting (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)phthalimide (by recrystallization from hexane, it is separated into an E form and a Z form, m.p. 106°-108° C.) is reacted with hydrazine to produce (E)-6,6-dimethyl-2-hepten-4-ynylamine. This compound is reductively alkylated by using equimolar proportions of 3-benzyloxybenzaldehyde and sodium borohydride in methanol to give the captioned compound.

Provenance & Evidence