Hydrochloric Acid → HCID 68961266, compound

HRID 2191843Notes

Reaction equation

HRID 2191843 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]=[CH:20][C:12]=1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl>C(OCC)(=O)C.CN(C)C=O>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:10][C:11]2[CH:23]=[C:22]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:21]=[CH:20][C:12]=2[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 96024-Fluorobenzyl chlorideHCID 11430Potassium CarbonateHCID 58508425Tert-butyl 3-amino-[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 68961266HCID 68961266, compoundYield 34.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To N,N-dimethylformamide 0.5 mL solution of 4-fluorobenzyl chloride 35 mg were added tert-butyl 2-amino-4-phenylbenzoate 54 mg and potassium carbonate 55 mg at room temperature, and it was stirred at 80° C. for 11 hours. After the reaction mixture was cooled to room temperature, sodium iodide 30 mg was added to it at room temperature, and it was stirred at 80° C. for 4 hours and 40 minutes. After the reaction mixture was cooled to room temperature, ethyl acetate and 1.0 mol/L hydrochloric acid 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=100:1] to give tert-butyl 2-(4-fluorobenzylamino)-4-phenylbenzoate 26 mg of a white solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. stirringit was stirred at 80° C. for 4 hours and 40 minutes
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. customThe organic layer was separated
  5. washafter washing with saturated sodium chloride aqueous solution
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c88e128451c44897b300713fa337ad4b
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

Loading…