Methylamine → 4-Methoxy-2-(2-methoxy-3-methylaminomethyl-phenoxy)-benzonitrile fumarate

HRID 1178503Notes

Reaction equation

HRID 1178503 reaction equation
[CH:1]([C:3]1[C:4]([O:20][CH3:21])=[C:5]([CH:17]=[CH:18][CH:19]=1)[O:6][C:7]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:8]=1[C:9]#[N:10])=O.CN.[C:24]([BH3-])#[N:25].[Na+].[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32]>C(O)(=O)C.CO>[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32].[CH3:16][O:15][C:13]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([O:6][C:5]2[CH:17]=[CH:18][CH:19]=[C:3]([CH2:1][NH:25][CH3:24])[C:4]=2[O:20][CH3:21])[CH:14]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 444972Fumaric AcidHCID 5003444Sodium cyanoborohydrideHCID 219303802-(3-Formyl-2-methoxy-phenoxy)4-methoxy-benzonitrile

Product 1

HCID 219303814-Methoxy-2-(2-methoxy-3-methylaminomethyl-phenoxy)-benzonitrile fumarateYield 60.5%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

2-(3-Formyl-2-methoxy-phenoxy)-4-methoxy-benzonitrile (0.38 g, 1.3 mmol), methylamine (2M in methanol, 3.0 mL, 6.0 mmol) and sodium cyanoborohydride (110 mg, 1.8 mmol) were stirred at ambient temperature in a 1% acetic acid/methanol solution (50 mL) for 17 h. The solvent was removed in vacuo. The residue was treated with 10% sodium carbonate solution and extracted with ethyl acetate. The ethyl acetate layer was to separated and fumaric acid (0.15 g, 1.3 mmol) was added. After the solvent was removed in vacuo, the residue was triturated with ethyl acetate overnight, collected by filtration, and dried to give 4-methoxy-2-(2-methoxy-3-methylaminomethyl-phenoxy)-benzonitrile fumarate (326 mg, 58%) as an off-white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. additionThe residue was treated with 10% sodium carbonate solution
  3. extractionextracted with ethyl acetate
  4. customto separated
  5. customAfter the solvent was removed in vacuo
  6. customthe residue was triturated with ethyl acetate overnight
  7. filtrationcollected by filtration
  8. customdried

Sources & evidence

ORD record
ord-1066d6df5f884296aebfb575a229f82c
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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