Phthalimide → HCID 19744579, compound

HRID 2254397Notes

Reaction equation

HRID 2254397 reaction equation
C1(=O)[NH:5]C(=O)C2=CC=CC=C12.Br[CH2:13][CH:14]=[CH:15][C:16]#[C:17][C:18]([CH3:21])([CH3:20])[CH3:19]>CN(C)C=O>[CH3:19][C:18]([CH3:21])([CH3:20])[C:17]#[C:16]/[CH:15]=[CH:14]/[CH2:13][NH2:5]

Participants

4

Reactant 2

HCID 6809PhthalimideHCID 454895941-Bromo-6,6-dimethylhept-2-en-4-yne

Product 1

HCID 19744579HCID 19744579, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  1. additiona mixture of E and Z forms in a ratio of about 3:1)
  2. customThe resulting (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)phthalimide (by recrystallization from hexane, it
  3. customis separated into an E form
  4. customa Z form, m.p. 106°-108° C.) is reacted with hydrazine

Sources & evidence

ORD record
ord-0f13ea46c39d44a1a25abac0838ac614
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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