Veratrylamine → HCID 714966, compound

HRID 339655Notes

Reaction equation

HRID 339655 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6]N.[C:13]([BH3-])#[N:14].[Na+]>CO.C1COCC1.C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6][NH:14][CH2:13][C:8]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:10]([O:11][CH3:12])[CH:9]=1

Participants

6

Reactant 2

HCID 79832VeratrylamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 714966HCID 714966, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,4-dimethoxybenzaldelyde (1 g, 6 mmol) in anhydrous methanol (10 ml) was added 3,4-dimethoxybenzylamine (1 g, 5.9 mmol) and the solution stirred under nitrogen at room temperature for 3 hours. The methanol was removed under reduced pressure to afford the crude imine, 1.9 g. The imine was dissolved in THF (10 ml) and acetic acid (4 ml), and sodium cyanoborohydride (0.38 g, 6 mmol) was added portionwise over 30 minutes. The solution was stirred for an additional 30 minutes at room temperature, and the solvents were removed under reduced pressure. The residue was neutralized with saturated aqueous sodium hydrogen carbonate, and the solid crude product was isolated by filtration, and dried under vacuum at 50° C. overnight, yield 0.6 g.

Workup

  1. customThe methanol was removed under reduced pressure
  2. customto afford the crude imine, 1.9 g
  3. stirringThe solution was stirred for an additional 30 minutes at room temperature
  4. customthe solvents were removed under reduced pressure
  5. customthe solid crude product was isolated by filtration
  6. customdried under vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-9310f863ea4e46d89db0da9cd3b8f738
Source dataset
uspto-grants-2014_11
Patent number
US08895554B2

Reaction notes

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