Sodium Bicarbonate → 2-(3,4-Dimethoxy-phenyl)-N-[3-(3,4-dimethoxy-phenyl)-propyl]-acetamide

HRID 458782Notes

Reaction equation

HRID 458782 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][NH2:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH2:25][C:26](Cl)=[O:27])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24].C([O-])(O)=O.[Na+]>C1COCC1>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH2:25][C:26]([NH:14][CH2:13][CH2:12][CH2:11][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:27])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 22810533,4-DimethoxybenzenepropanamineHCID 3604458(3,4-Dimethoxyphenyl)acetyl chloride

Product 1

HCID 122679872-(3,4-Dimethoxy-phenyl)-N-[3-(3,4-dimethoxy-phenyl)-propyl]-acetamideYield 53.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-(3,4-dimethoxy-phenyl)-propylamine (12.51 g, 64.06 mmol) and TEA (10 ml, 71.84 mmol) in anhydrous THF (70 ml) was cooled to 0° C. and (3,4-dimethoxy-phenyl)-acetyl chloride (13.75 g, 64.07 mmol) in THF (28 ml) was added dropwise. After stirring at RT for 13 h under nitrogen, a saturated aqueous NaHCO3 solution was added and the reaction mixture was extracted three times with AcOEt. The organic phase was dried over anhydrous MgSO4, filtered and the solvent was removed in vacuo. A subsequent washing of the crude solid with toluene gave the title compound (12.81 g, 34.30 mmol, 53%) as a beige solid.

Workup

  1. extractionthe reaction mixture was extracted three times with AcOEt
  2. dry with materialThe organic phase was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. washA subsequent washing of the crude solid with toluene

Sources & evidence

ORD record
ord-e6e0f43bcba842739e83509c21b31b2a
Source dataset
uspto-grants-2007_03
Patent number
US07192950B2

Reaction notes

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