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

HRID 458790Notes

Reaction equation

HRID 458790 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][NH2:18])=[CH:11][C:10]=1[O:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:31][C:32](Cl)=[O:33])[CH:26]=[CH:27][C:28]=1[O:29][CH3:30].C([O-])(O)=O.[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][NH:18][C:32](=[O:33])[CH2:31][C:25]2[CH:26]=[CH:27][C:28]([O:29][CH3:30])=[C:23]([O:22][CH3:21])[CH:24]=2)=[CH:11][C:10]=1[O:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 3604458(3,4-Dimethoxyphenyl)acetyl chlorideHCID 123732973-[4-(Benzyloxy)-3-methoxyphenyl]propan-1-amine

Product 1

HCID 18442596N-[3-(4-Benzyloxy-3-methoxy-phenyl)-propyl]-2-(3,4-dimethoxy-phenyl)-acetamideYield 65.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-(4-benzyloxy-3-methoxy-phenyl)-propylamine (6.06 g, 22.36 mmol) and TEA (3.5 ml, 25.14 mmol) in anhydrous THF (25 ml) was cooled to 0° C. and (3,4-dimethoxy-phenyl)-acetyl chloride (4.80 g, 22.36 mmol) in THF (10 ml) was added dropwise. After stirring at RT for 28 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 (6.57 g, 14.61 mmol, 65%) 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-f98729d72eff4572bd0958ba36760db3
Source dataset
uspto-grants-2007_03
Patent number
US07192950B2

Reaction notes

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