Hydrochloric Acid → HCID 57667997, compound

HRID 2191696Notes

Reaction equation

HRID 2191696 reaction equation
I[C:2]1[CH:10]=[C:9]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:19]([NH2:27])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+].Cl>[Cu]I.C(OCC)(=O)C.CS(C)=O>[CH2:11]([C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([NH:27][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:10]=1)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 1001PhenethylamineHCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 57667811HCID 57667811, compound

Product 1

HCID 57667997HCID 57667997, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To dimethylsulfoxide 2.0 mL solution of 2-iodo-4-phenethylbenzoic acid 0.20 g were added phenethylamine 0.11 mL, copper (I) iodide 0.010 g, proline 0.013 g and potassium carbonate 0.16 g, and it was stirred at 60° C. for 4 hours. After the reaction mixture was cooled to room temperature, 1.0 mol/L hydrochloric acid and ethyl acetate were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent; hexane:ethyl acetate:acetic acid=90:10:1] to give 4-phenethyl-2-(phenethylamino)benzoic acid 0.12 g of white solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washafter washing with saturated sodium chloride aqueous solution
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5232c4d769564b96bad2264d7d53b74b
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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