Water → HCID 86746360, compound

HRID 373936Notes

Reaction equation

HRID 373936 reaction equation
[CH3:1][N:2]([CH:15](Cl)[CH:16]([CH3:18])C)[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1.[C-:20]#[N:21].[K+].C1OCCOCCOCCOCCOCCOC1.O>C(#N)C>[CH3:1][N:2]([CH:15]([CH2:16][CH3:18])[C:20]#[N:21])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 86746359HCID 86746359, compound

Product 1

HCID 86746360HCID 86746360, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.67 g of 3-((N-methyl-N-(2-(3,4-dimethoxyphenyl)ethyl)-amino-2-methylpropyl chloride was dissolved in 40 ml of acetonitrile, followed by the addition of 2.13 g of potassium cyanide and 0.1 g of 18-crown-6. The obtained mixture was heated under reflux for 40 hours, followed by the addition of water. The obtained mixture was extracted with ethyl acetate. The ethyl acetate phase was washed with water and a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and distilled to remove the solvent. The residue was purified by silica gel column chromatography [solvent: n-hexane/ethyl acetate (1:1)] to obtain 3.93 g of the title compound as a pale yellow oil (yield: 87%).

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for 40 hours
  3. extractionThe obtained mixture was extracted with ethyl acetate
  4. washThe ethyl acetate phase was washed with water
  5. dry with materiala saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate
  6. distillationdistilled
  7. customto remove the solvent
  8. customThe residue was purified by silica gel column chromatography [solvent: n-hexane/ethyl acetate (1:1)]

Sources & evidence

ORD record
ord-e26045558b594636b28418cfa892c60b
Source dataset
uspto-grants-1992_11
Patent number
US05166188

Reaction notes

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