Methylamine → HCID 21930354, compound

HRID 1178531Notes

Reaction equation

HRID 1178531 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]([F:17])=[C:13]([CH2:18]Cl)[CH:12]=2)[CH:3]=1.[CH3:20][NH2:21].[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26]>C(O)C.CO>[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26].[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]([F:17])=[C:13]([CH2:18][NH:21][CH3:20])[CH:12]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 444972Fumaric AcidHCID 21930355HCID 21930355, compound

Product 1

HCID 21930354HCID 21930354, compoundYield 104.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of 4-chloro-2-(3-chloromethyl-4-fluorophenoxy)-benzonitrile (0.14 g, 0.47 mmol) in ethanol (15 mL) was added methylamine (33% in ethanol, 4.0 mL, 32 mmol), and the reaction mixture stirred for 10 days at ambient temperature. 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 a solution of fumaric acid (50 mg, 0.43 mmol) in methanol (3 mL) was added. After the solvent was removed in vacuo, the residue was triturated with diethyl ether overnight, collected by filtration, and dried to give 4-chloro-2-(4-fluoro-3-methylaminomethyl-phenoxy)-benzonitrile fumarate (183 mg, 95%) 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 diethyl ether overnight
  7. filtrationcollected by filtration
  8. customdried

Sources & evidence

ORD record
ord-63e1ed35d56b42399f919728d3fe6fcf
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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