Carbon Dioxide → N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-methyl-3,4,5,6-tetrahydrophthalamide

HRID 742416Notes

Reaction equation

HRID 742416 reaction equation
Cl.[CH3:2][NH2:3].C(=O)([O-])[O-].[K+].[K+].C(=O)=O.[F:13][C:14]1[CH:19]=[C:18]([Cl:20])[C:17]([O:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:16][C:15]=1[N:27]1[C:31](=[O:32])[C:30]2[CH2:33][CH2:34][CH2:35][CH2:36][C:29]=2[C:28]1=[O:37]>C(#N)C>[F:13][C:14]1[CH:19]=[C:18]([Cl:20])[C:17]([O:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:16][C:15]=1[NH:27][C:28](=[O:37])[C:29]1[CH2:36][CH2:35][CH2:34][CH2:33][C:30]=1[C:31]([NH:3][CH3:2])=[O:32]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 11430Potassium CarbonateHCID 6364545Methylamine hydrochlorideHCID 15279390N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydrophthalimide

Product 1

HCID 19425267N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-methyl-3,4,5,6-tetrahydrophthalamideYield 74.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methylamine hydrochloride (1.70 g, 24.8 mmol) and potassium carbonate (1.70 g, 12.3 mmol), and acetonitrile (5 ml) as a solvent were placed into a round bottom flask (100 cc), followed by stirring at room temperature. After confirming the generation of carbon dioxide gas, N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydrophthalimide (5.88 g, 16.2 mmol) was added thereto, followed by stirring at room temperature for 4 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the precipitated crystals were isolated by filtration. The crystals were washed with hexane and dried to obtain N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-methyl-3,4,5,6-tetrahydrophthalamide as white crystals (4.79 g, 74.9% yield).

Workup

  1. additionwas added
  2. stirringby stirring at room temperature for 4 hours
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe precipitated crystals were isolated by filtration
  6. washThe crystals were washed with hexane
  7. customdried

Sources & evidence

ORD record
ord-35317fcec12c477494b8d1a0edbda808
Source dataset
uspto-grants-1996_09
Patent number
US05554581

Reaction notes

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