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

HRID 1243688Notes

Reaction equation

HRID 1243688 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]=O)=[C:13](OC)[CH:12]=2)[CH:3]=1.CN.[C:23]([BH3-])#[N:24].[Na+].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31]>C(OCC)(=O)C.C(O)(=O)C.CO>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31].[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:17][NH:24][CH3:23])=[CH:15][C:16]=2[O:31][CH3:30])[CH:3]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 444972Fumaric AcidHCID 5003444Sodium cyanoborohydrideHCID 219303894-Chloro-2-(4-formyl-3-methoxy-phenoxy)-benzonitrile

Product 1

HCID 219303444-Chloro-2-(2-methoxy-4-methylaminomethyl-phenoxy)-benzonitrile fumarateYield 109.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 10129899Acetic acid methanolSolvent

Procedure

4-Chloro-2-(4-formyl-3-methoxy-phenoxy)-benzonitrile (0.93 g, 3.2 mmol), methylamine (2M in methanol, 4.8 ml, 9.6 mmol) and sodium cyanoborohydride (0.22 g, 3.6 mmol) were stirred at ambient temperature in a 1% acetic acid/methanol solution (125 ml) for 20 h. The solvent was removed in vacuo. The residue was treated with 10% aqueous sodium carbonate and extracted with ethyl acetate. Fumaric acid (0.40 g, 3.4 mmol) was added to the separated ethyl acetate layer and the solvent removed in vacuo. The residue was triturated with ethyl acetate overnight, filtered and dried to give 4-chloro-2-(2-methoxy-4-methylaminomethyl-phenoxy)-benzonitrile fumarate (782 mg, 58%) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. additionThe residue was treated with 10% aqueous sodium carbonate
  3. extractionextracted with ethyl acetate
  4. customthe solvent removed in vacuo
  5. customThe residue was triturated with ethyl acetate overnight
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-c365485da2b144a3ae07af0eb4f39e27
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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