4-Methylmorpholine → HCID 22417591, compound

HRID 1720422Notes

Reaction equation

HRID 1720422 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]1[C:20](=[O:21])C2CCCC(=C2)C1=O.[F:26][C:27]([F:39])([F:38])[C:28]1[CH:29]=[C:30]([CH:35]=[CH:36][CH:37]=1)[C:31]([NH2:34])([CH3:33])[CH3:32].CN1[CH2:46][CH2:45][O:44]CC1>C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)=[CH:4][C:3]=1[NH:15][C:20](=[O:21])[C:6]1[CH2:7][CH2:2][CH2:3][CH2:4][C:46]=1[C:45]([NH:34][C:31]([C:30]1[CH:35]=[CH:36][CH:37]=[C:28]([C:27]([F:38])([F:39])[F:26])[CH:29]=1)([CH3:33])[CH3:32])=[O:44]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 19425191N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydroisophthalimideHCID 194252732-[3-(Trifluoromethyl)phenyl]propan-2-amine

Product 1

HCID 22417591HCID 22417591, compoundYield 46.2%

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-trifluoromethylcumylamine (0.730 g, 3.59 mmol), N-methylmorpholine (0.320 g, 3.16 mmol), and benzene (15 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 chloroform/acetone to obtain N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-(3-trifluoromethylcumyl)-3,4,5,6-tetrahydrophthalamide as white crystals (0.360 g, 23.1% 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 chloroform/acetone

Sources & evidence

ORD record
ord-421e48d56d824a4288b06d529a96ea0a
Source dataset
uspto-grants-1996_04
Patent number
US05506190

Reaction notes

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