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

HRID 742424Notes

Reaction equation

HRID 742424 reaction equation
Cl.[CH3:2][NH2:3].[C:4](=[O:7])([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:32](=[O:33])C2CCCC(=C2)C1=O.Cl>C(#N)C>[F:13][C:14]1[CH:19]=[C:18]([Cl:20])[C:17]([O:21][CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26]2)=[CH:16][C:15]=1[NH:27][C:32](=[O:33])[C:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=1[C:4]([NH:3][CH3:2])=[O:7]

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 6364545Methylamine hydrochlorideHCID 19425191N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydroisophthalimide

Product 1

HCID 19425267N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-methyl-3,4,5,6-tetrahydrophthalamideYield 107.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methylamine hydrochloride (0.200 g, 2.96 mmol) and potassium carbonate (0.400 g, 2.89 mmol), and acetonitrile (5 ml) as a solvent were placed into a round bottom flask (25 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-tetrahydroisophthalimide (0.650 g, 1.79 mmol) was added thereto, followed by stirring overnight at room temperature. After completion of the reaction, the reaction mixture was poured into 1N hydrochloric acid (20 ml), and the mixture was extracted with ethyl acetate (40 ml×3 portions). After drying the organic layer over anhydrous magnesium sulfate, the drying agent was removed, and the solvent was distilled off under reduced pressure. The precipitated crystals were isolated by filtration, thoroughly washed with hexane and dried to obtain N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-methyl-3,4,5,6-tetrahydrophthalamide as white crystals (0.380 g, 53.8% yield). The melting point and the spectral data thereof are shown in Example 37.

Workup

  1. additionwas added
  2. stirringby stirring overnight at room temperature
  3. customAfter completion of the reaction
  4. extractionthe mixture was extracted with ethyl acetate (40 ml×3 portions)
  5. dry with materialAfter drying the organic layer over anhydrous magnesium sulfate
  6. customthe drying agent was removed
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe precipitated crystals were isolated by filtration
  9. washthoroughly washed with hexane
  10. customdried

Sources & evidence

ORD record
ord-1b32a56387f6467387b71f463e860bc1
Source dataset
uspto-grants-1996_09
Patent number
US05554581

Reaction notes

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