Hydrochloric Acid → N-(4-Chlorophenoxyethyl)-3-(2-methoxyphenyl)propanamide

HRID 350830Notes

Reaction equation

HRID 350830 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][C:11]([OH:13])=O.[Cl:14][C:15]1[CH:24]=[CH:23][C:18]([O:19][CH2:20][CH2:21][NH2:22])=[CH:17][CH:16]=1.CCN=C=NCCCN(C)C.Cl.Cl>O1CCCC1.C(Cl)Cl>[Cl:14][C:15]1[CH:24]=[CH:23][C:18]([O:19][CH2:20][CH2:21][NH:22][C:11](=[O:13])[CH2:10][CH2:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 806523-(o-Methoxyphenyl)propionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27941912-(4-Chlorophenoxy)ethylamine

Product 1

HCID 21055042N-(4-Chlorophenoxyethyl)-3-(2-methoxyphenyl)propanamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(2-Methoxyphenyl)propionic acid (8.3 g, 46.2 mmol) was dissolved in tetrahydrofuran (20 mL), and 4-chlorophenoxyethylamine (10.3 g, 60.0 mmol) was added dropwise thereto at room temperature. Subsequently, a solution (10 mL) of WSC•HCl (11.5 g, 60.0 mmol) in methylene chloride was slowly added dropwise thereto under ice-cooling, followed by stirring overnight. Under ice cooling, diluted hydrochloric acid was added dropwise thereto, followed by extraction with chloroform. The organic layer was washed with brine, and the resultant mixture was subjected to drying over anhydrous sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (chloroform/methanol=20/1), whereby the target compound was obtained (12.8 g, 83%).

Workup

  1. customat room temperature
  2. temperatureunder ice-cooling
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialto drying over anhydrous sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (chloroform/methanol=20/1), whereby the target compound
  6. customwas obtained (12.8 g, 83%)

Sources & evidence

ORD record
ord-f87c91c6252b4a1cad701bbfbf389194
Source dataset
uspto-grants-2007_02
Patent number
US07183295B2

Reaction notes

Loading…