Potassium Carbonate → (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-phthalimidobenzylamine

HRID 2254470Notes

Reaction equation

HRID 2254470 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]3[C:10]2=[O:19])[CH:6]=[CH:7][CH:8]=1.Cl.[CH2:21]([NH:23][CH2:24]/[CH:25]=[CH:26]/[C:27]#[C:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH3:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:30][C:29]([CH3:31])([CH3:32])[C:28]#[C:27]/[CH:26]=[CH:25]/[CH2:24][N:23]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]3[C:10]2=[O:19])[CH:4]=1)[CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3340982-[3-(Bromomethyl)phenyl]-1H-isoindole-1,3(2H)-dioneHCID 19917114(E)-N-ethyl-6,6-dimethyl-2-hepten-4-ynylamine hydrochloride

Product 1

HCID 19744709(E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-phthalimidobenzylamineYield 72.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.0 g of N-(3-bromomethylphenyl)phthalimide [synthesized by brominating N-(m-tolyl)phthalimide with N-bromosuccinimide in carbon tetrachloride] was dissolved in 100 ml of dimethylformamide, and 3.82 g of (E)-N-ethyl-6,6-dimethyl-2-hepten-4-ynylamine hydrochloride and 7.87 g of potassium carbonate were added. The mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was extracted with ethyl acetate-water and the organic layer was separated, and the solvent was evaporated, and then the residue was washed with a small amount of ethyl ether to give 5.5 g (yield 72%) of (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-phthalimidobenzylamine, m.p. 96°-98 ° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate-water
  3. customthe organic layer was separated
  4. customthe solvent was evaporated
  5. washthe residue was washed with a small amount of ethyl ether

Sources & evidence

ORD record
ord-1a9d09d2064f4de88b3e2273b57475b9
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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