Benzaldehyde → Methyl 4'-[2-(benzylamino)ethyl]-1,1'-biphenyl-4-carboxylate

HRID 1866179Notes

Reaction equation

HRID 1866179 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClCCl>[CH2:21]([NH:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:12]=2)=[CH:9][CH:10]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 22171302Methyl 4'-(2-aminoethyl)-1,1'-biphenyl-4-carboxylate hydrochloride

Product 1

HCID 22171573Methyl 4'-[2-(benzylamino)ethyl]-1,1'-biphenyl-4-carboxylateYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4′-(2-aminoethyl)-1,1′-biphenyl-4-carboxylate hydrochloride (420 mg) and benzaldehyde (153 mg) in dichloromethane (5 ml) was stirred for 3 hours, and the mixture was evaporated in vacuo. To the residue in methanol (10 ml) was added sodium borohydride (65 mg) on ice cooling, and stirred at the same temperature for 1 hour. The resulting mixture was poured into saturated aqueous sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed (hexane-ethyl acetate) over silica gel to afford methyl 4′-[2-(benzylamino)ethyl]-1,1′-biphenyl-4-carboxylate (460 mg) as a colorless powder.

Workup

  1. customthe mixture was evaporated in vacuo
  2. additionTo the residue in methanol (10 ml) was added sodium borohydride (65 mg) on ice cooling
  3. additionThe resulting mixture was poured into saturated aqueous sodium bicarbonate solution
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was chromatographed (hexane-ethyl acetate) over silica gel

Sources & evidence

ORD record
ord-ada1e733d98144ae85c4064ce5df2061
Source dataset
uspto-grants-2009_12
Patent number
US07629366B2

Reaction notes

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