Dimethylamine → HCID 21930342, compound

HRID 1178489Notes

Reaction equation

HRID 1178489 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][CH:14]=[C:13]([CH:17]=O)[CH:12]=2)[CH:3]=1.[CH3:19][NH:20][CH3:21].C([BH3-])#N.[Na+].[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30]>C(O)(=O)C.CO>[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30].[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][CH:14]=[C:13]([CH2:17][N:20]([CH3:21])[CH3:19])[CH:12]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 444972Fumaric AcidHCID 5003444Sodium cyanoborohydrideHCID 11149570HCID 11149570, compound

Product 1

HCID 21930342HCID 21930342, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

4-Chloro-2-(3-formylphenoxy)benzonitrile (0.20 g, 0.78 mmol), dimethylamine (2M in methanol, 1.0 mL, 2.0 mmol) and sodium cyanoborohydride (60 mg, 0.96 mmol) were stirred at ambient temperature in a 1% acetic acid/methanol solution (20 mL) for 18 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 separated and fumaric acid (0.10 g, 0.86 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-chloro-2-[3-(dimethylaminomethyl)phenoxy]benzonitrile fumarate (179 mg, 58%) as a 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. customThe ethyl acetate layer was 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-4c512ca3ed8441af9668b2beb51f29d9
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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