1-(Pyridin-3-yl)ethan-1-amine → (6,4'-Dimethoxy-biphenyl-3-ylmethyl)-(1-pyridin-3-yl-ethyl)amine

HRID 460141

Reaction equation

HRID 460141 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([NH2:9])[CH3:8])[CH:2]=1.[CH3:10][O:11][C:12]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:16][C:15]([CH:26]=O)=[CH:14][CH:13]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH3:10][O:11][C:12]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:16][C:15]([CH2:26][NH:9][CH:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH3:8])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 27716881-(Pyridin-3-yl)ethan-1-amineHCID 5049666Sodium triacetoxyborohydrideHCID 223911916,4'-Dimethoxybiphenyl-3-carbaldehyde

Product 1

HCID 22391323(6,4'-Dimethoxy-biphenyl-3-ylmethyl)-(1-pyridin-3-yl-ethyl)amineYield 50%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

1-Pyridin-3-yl-ethylamine (245 mg, 2 mmol) and 6,4′-Dimethoxy-biphenyl-3-carbaldehyde (121 mg, 0.5 mmol) were dissolved in dichloroethane (10 mL). After stirring for 6 h at room temperature, the sodium triacetoxyborohydride (212 mg, 1.0 mmol, Aldrich) was added to the solution at 0 C. The mixture was stirred under nitrogen at room temperature for overnight then the reaction was cooled at ice bath and quenched with saturated aqueous sodium bicarbonate (10 mL). The organic phase was separated and the aqueous phase was extracted with dichloroethane (10 mL×3). The combined organic layers were dried over anhydrous magnesium sulfate and concentrated via vacuo. The crude was purified by column chromatography (silica gel, ethyl acetate) to give the title compound as white solid in 50% yield (87 mg, 0.25 mmol).

Workup

  1. stirringThe mixture was stirred under nitrogen at room temperature for overnight
  2. temperaturethe reaction was cooled at ice bath
  3. customquenched with saturated aqueous sodium bicarbonate (10 mL)
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted with dichloroethane (10 mL×3)
  6. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  7. concentrationconcentrated via vacuo
  8. customThe crude was purified by column chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-6eb08a0910f14b3eac3200d70a650fab
Source dataset
uspto-grants-2007_03
Patent number
US07196102B2

Linked notes

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