Hydrochloric Acid → Ethyl 4'-(3-aminopropyl)-1,1'-biphenyl-4-carboxylate

Reaction equation

FC(F)(F)C([NH:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)=O.Cl.[CH2:28](O)C>>[NH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([O:23][CH2:24][CH3:28])=[O:22])=[CH:19][CH:20]=2)=[CH:13][CH:14]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 702Ethanol2×

HCID 22171344Methyl 4'-[3-[(trifluoroacetyl)amino]propyl]-1,1'-biphenyl-4-carboxylate

Product 1

HCID 22171365Ethyl 4'-(3-aminopropyl)-1,1'-biphenyl-4-carboxylate

Procedure

A mixture of methyl 4′-[3-[(trifluoroacetyl)amino]-propyl]-1,1′-biphenyl-4-carboxylate (920 mg), 4N hydrochloride in ethanol (2 ml) and ethanol (2 ml) was refluxed for 18 hours. The mixture was evaporated in vacuo. The residue was diluted with ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel (chloroform:methanol=100:1) to give ethyl 4′-(3-aminopropyl)-1,1′-biphenyl-4-carboxylate (200 mg) as a colorless foam.