Imidazole → (E,E)-N-methyl-N-(6,6-dimethyl-2-hepten-4-ynyl)-3-[4-(1-imidazolyl)-2-butenyloxy]benzylamine

HRID 1464745Notes

Reaction equation

HRID 1464745 reaction equation
[CH3:1][N:2]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20]/[CH:21]=[CH:22]/[CH2:23]Cl)[CH:14]=1)[CH2:3]/[CH:4]=[CH:5]/[C:6]#[C:7][C:8]([CH3:11])([CH3:10])[CH3:9].[NH:25]1[CH:29]=[CH:28][N:27]=[CH:26]1>CN(C)C=O>[CH3:1][N:2]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20]/[CH:21]=[CH:22]/[CH2:23][N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)[CH:14]=1)[CH2:3]/[CH:4]=[CH:5]/[C:6]#[C:7][C:8]([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 19916973(E,E)-N-methyl-N-(6,6-dimethyl-2-hepten-4-ynyl)-3-(4-chloro-2-butenyloxy)benzylamine

Product 1

HCID 19917065(E,E)-N-methyl-N-(6,6-dimethyl-2-hepten-4-ynyl)-3-[4-(1-imidazolyl)-2-butenyloxy]benzylamineYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

50 mg of (E,E)-N-methyl-N-(6,6-dimethyl-2-hepten-4-ynyl)-3-(4-chloro-2-butenyloxy)benzylamine was dissolved in 0.5 ml of dimethylformamide, and 30 mg of imidazole was added. The mixture was heated at 80° C. for 1 hour. The solvent was evaporated under reduced pressure, and ethyl acetate and water were added to the residue to extract it. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The desiccant was separated by filtration, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography [ethyl acetate→ethyl acetate/methanol=10/1] to give 27 mg (yield 53 %) of the captioned compound as a pale yellow oil.

Workup

  1. customThe solvent was evaporated under reduced pressure, and ethyl acetate and water
  2. additionwere added to the residue
  3. extractionto extract it
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe desiccant was separated by filtration
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography [ethyl acetate→ethyl acetate/methanol=10/1]

Sources & evidence

ORD record
ord-2e51db46d6cd459cbb9d996a4082535c
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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