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

HRID 1720418Notes

Reaction equation

HRID 1720418 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].[F:26][C:27]1[CH:36]=[CH:35][C:30]([C:31]([NH2:34])([CH3:33])[CH3:32])=[CH:29][CH:28]=1.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:34][C:31]([C:30]1[CH:29]=[CH:28][C:27]([F:26])=[CH:36][CH:35]=1)([CH3:33])[CH3:32])=[O:41]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 130256651-(4-Fluorophenyl)-1-methylethylamineHCID 19425191N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydroisophthalimide

Product 1

HCID 22417586N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-(4-fluorocumyl)-3,4,5,6-tetrahydrophthalamideYield 58.7%

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), 4-fluorocumylamine (0.600 g, 3.92 mmol), N-methylmorpholine (0.330 g, 3.26 mmol), and benzene (10 ml) as a solvent were placed into a round bottom flask (50 cc) and stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting crude product was recrystallized from ethyl acetate/acetone to obtain N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-(4-fluorocumyl)-3,4,5,6-tetrahydrophthalamide as white crystals (0.417 g, 29.3% yield).

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe resulting crude product was recrystallized from ethyl acetate/acetone

Sources & evidence

ORD record
ord-afd427aa053d4873b0ffa2685dd89f3f
Source dataset
uspto-grants-1996_04
Patent number
US05506190

Reaction notes

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