Triethylamine → HCID 12051144, compound

HRID 428123Notes

Reaction equation

HRID 428123 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([CH2:9][CH2:10][NH2:11])=[CH:7][CH:6]=1.[C:14]([CH2:16][C:17](O)=[O:18])#[N:15].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:14]([CH2:16][C:17]([NH:11][CH2:10][CH2:9][C:8]1[CH:12]=[CH:13][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:6][CH:7]=1)=[O:18])#[N:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9740Cyanoacetic acidHCID 516892Sodium BicarbonateHCID 12051143HCID 12051143, compound

Product 1

HCID 12051144HCID 12051144, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Methoxymethoxyphenethylamine (1.58 g, 8.7 mmol) and cyanoacetic acid (0.82 g, 9.6 mmol) were dissolved in dimethylformamide (10 ml) and under ice-cooling and stirring diethylphosphoric cyanide (1.51 ml, 9.6 mmol) and triethylamine (1.34 ml, 9.6 mmol) were sequentially added. After stirring at room temperature for 24 hours, saturated aqueous sodium bicarbonate solution was added to the reaction mixture, extracted with ethyl acetate, washed with water and dried over magnesium sulfate. The solvent was distilled out under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=19:1) to yield 2-cyano-N-(4-methoxymethoxyphenethyl)acetamide (0.97 g, 45%).

Workup

  1. temperaturecooling
  2. additionwere sequentially added
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled out under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-9261baaf781a448dae16f2111f2294af
Source dataset
uspto-grants-2001_11
Patent number
US06313153B1

Reaction notes

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