4-Methylmorpholine → N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-(3-chlorocumyl)-3,4,5,6-tetrahydrophthalamide

HRID 1720420Notes

Reaction equation

HRID 1720420 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][C:3]=1[N:15]1C(=O)C2CCCC(=C2)[C:16]1=[O:25].[Cl:26][C:27]1[CH:28]=[C:29]([CH:34]=[CH:35][CH:36]=1)[C:30]([NH2:33])([CH3:32])[CH3:31].CN1[CH2:43][CH2:42][O:41]CC1>C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][C:3]=1[NH:15][C:16](=[O:25])[C:6]1[CH2:7][CH2:2][CH2:3][CH2:4][C:43]=1[C:42]([NH:33][C:30]([C:29]1[CH:34]=[CH:35][CH:36]=[C:27]([Cl:26])[CH:28]=1)([CH3:32])[CH3:31])=[O:41]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 135695212-(3-Chlorophenyl)propan-2-amineHCID 19425191N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydroisophthalimide

Product 1

HCID 19425271N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-(3-chlorocumyl)-3,4,5,6-tetrahydrophthalamideYield 117.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-(2-Fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydroisophthalimide (1.00 g, 2.75 mmol), 3-chlorocumylamine (0.630 g, 3.71 mmol), N-methylmorpholine (0.670 g, 6.62 mmol), and benzene (10 ml) as a solvent were placed into a round bottom flask (50 cc) and stirred overnight at room temperature, followed by heating at 50° C. for 7 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'-(3-chlorocumyl)-3,4,5,6-tetrahydrophthalamide as white crystals (0.859 g, 58.6% yield).

Workup

  1. temperatureby heating at 50° C. for 7 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe precipitated crystals were isolated by filtration
  5. washThe crystals were washed with hexane
  6. customdried

Sources & evidence

ORD record
ord-47991d0ba3cb4275a327f14a4f0fd65e
Source dataset
uspto-grants-1996_04
Patent number
US05506190

Reaction notes

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