3-Methoxybenzylamine → HCID 64389025, compound

HRID 525460Notes

Reaction equation

HRID 525460 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][NH2:10])[CH:6]=[CH:7][CH:8]=1.[CH3:11][O:12][CH:13]([O:17][CH3:18])[C:14](=O)[CH3:15].S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[CH3:11][O:12][CH:13]([O:17][CH3:18])[CH:14]([NH:10][CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:15]

Participants

6

Reactant 4

HCID 211563-MethoxybenzylamineHCID 24436Sodium SulfateHCID 80650Pyruvic aldehyde dimethyl acetalHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 64389025HCID 64389025, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(3-Methoxyphenyl) methanamine (100 g, 730 mmol, 1 equiv.) and 1,1-dimethoxypropan-2-one (172.2 g, 1.46 mol, 2 equiv.) were dissolved in acetic acid (1.8 L). Anhydrous sodium sulfate (207 g, 1.46 mol, 2 equiv.) was added. The mixture was stirred for 1.5 hour at room temperature. Sodium triacetoxyborohydride (463 g, 2.19 mmol, 3 equiv.) was added in portions over 40 minutes. The mixture was stirred for an additional 2 hours. Most of the acetic acid was removed under reduced pressure. The resulting black oil was dissolved in ethyl acetate (2 L) and saturated aqueous sodium bicarbonate (1 L) was added slowly followed by solid potassium carbonate to adjust the pH to 7. The organic layer was separated, dried over sodium sulfate and filtered. The filtrate was concentrated under reduce pressure to give a black oil which was purified by silica gel chromatography to give the title compound (120 g, ˜85% purity by LC/MS, 68% yield).

Workup

  1. stirringThe mixture was stirred for an additional 2 hours
  2. customMost of the acetic acid was removed under reduced pressure
  3. dissolutionThe resulting black oil was dissolved in ethyl acetate (2 L)
  4. additionsaturated aqueous sodium bicarbonate (1 L) was added slowly
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customto give a black oil which
  10. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-a8c56c5056c0471b94e55adf2df91409
Source dataset
uspto-grants-2016_05
Patent number
US09340527B2

Reaction notes

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