Hydrochloric Acid → HCID 19425216, compound

HRID 1720423Notes

Reaction equation

HRID 1720423 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.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([NH2:37])([CH3:36])[CH2:34][CH3:35])=[CH:29][CH:28]=1.CN1[CH2:44][CH2:43][O:42]CC1.Cl>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:20](=[O:21])[C:6]1[CH2:7][CH2:2][CH2:3][CH2:4][C:44]=1[C:43]([NH:37][C:33]([C:30]1[CH:29]=[CH:28][C:27]([Cl:26])=[CH:32][CH:31]=1)([CH3:36])[CH2:34][CH3:35])=[O:42]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 19425191N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydroisophthalimideHCID 2020814587649-89-6

Product 1

HCID 19425216HCID 19425216, compoundYield 39.6%

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), 1-(4-chlorophenyl)-1-methylpropylamine (0.760 g, 4.14 mmol), N-methylmorpholine (0.310 g, 3.06 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 reaction mixture was poured into 2N hydrochloric acid (30 ml), and the mixture was extracted with ethyl acetate (30 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 resulting crude product was recrystallized from ethyl acetate/acetone to obtain N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-(1-(4-chlorophenyl)-1-methylpropyl}-3,4,5,6-tetrahydrophthalamide as white crystals (0.298 g, 19.8% yield).

Workup

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with ethyl acetate (30 ml×3 portions)
  3. dry with materialAfter drying the organic layer over anhydrous magnesium sulfate
  4. customthe drying agent was removed
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting crude product was recrystallized from ethyl acetate/acetone

Sources & evidence

ORD record
ord-f60ae1f14566439ab5e6d05bb7b0b608
Source dataset
uspto-grants-1996_04
Patent number
US05506190

Reaction notes

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