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

HRID 1866155Notes

Reaction equation

HRID 1866155 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

4

Reactant 3

HCID 313Hydrochloric AcidHCID 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.

Workup

  1. temperaturewas refluxed for 18 hours
  2. customThe mixture was evaporated in vacuo
  3. additionThe residue was diluted with ethyl acetate and saturated aqueous sodium bicarbonate solution
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-b43a577dcb5c4c3e8efaa010867fe860
Source dataset
uspto-grants-2009_12
Patent number
US07629366B2

Reaction notes

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