Acetic Acid → (6,4'-Dimethoxybiphenyl-3-ylmethyl)-(1-quinolin-4-yl-ethyl)-amine

HRID 460145

Reaction equation

HRID 460145 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]([NH2:13])[CH3:12])=[CH:3][CH:2]=1.[CH3:14][O:15][C:16]1[C:21]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[CH:20][C:19]([CH:30]=O)=[CH:18][CH:17]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH3:14][O:15][C:16]1[C:21]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[CH:20][C:19]([CH2:30][NH:13][CH:11]([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=[CH:2][CH:3]=2)[CH3:12])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 108449271-(Quinolin-4-yl)ethan-1-amineHCID 223911916,4'-Dimethoxybiphenyl-3-carbaldehyde

Product 1

HCID 22391337(6,4'-Dimethoxybiphenyl-3-ylmethyl)-(1-quinolin-4-yl-ethyl)-amineYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 1-quinolin-4-yl-ethylamine (510 mg, 3 mmol) and 6,4′-dimethoxy-biphenyl-3-carbaldehyde (242 mg, 1.0 mmol) were stirred with acetic acid (300 mg, J. T. Baker) in methyl alcohol (15 mL0 at room temperature for 4 h. To the reaction solution was added sodium cyanoborohydride (1.0 g, 16 mmol, Aldrich) 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 (30 mL). The methyl alcohol was removed from the mixture via vacuo. The residue was extracted by ethyl acetate (30 mL×4). The combined organic phases were dried over anhydrous magnesium sulfate and concentrated via vacuo. The title compound was purified by column chromatography (silica gel, ethyl acetate) in form as white solid in 72% yield (287 mg, 0.72 mmol).

Workup

  1. temperaturethe reaction was cooled at ice bath
  2. customquenched with saturated aqueous sodium bicarbonate (30 mL)
  3. customThe methyl alcohol was removed from the mixture via vacuo
  4. extractionThe residue was extracted by ethyl acetate (30 mL×4)
  5. dry with materialThe combined organic phases were dried over anhydrous magnesium sulfate
  6. concentrationconcentrated via vacuo
  7. customThe title compound was purified by column chromatography (silica gel, ethyl acetate) in form as white solid in 72% yield (287 mg, 0.72 mmol)

Sources & evidence

ORD record
ord-e31bc11dfb4b474c8aec9a14c75911e6
Source dataset
uspto-grants-2007_03
Patent number
US07196102B2

Linked notes

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