Benzene → HCID 19425286, compound

HRID 742406Notes

Reaction equation

HRID 742406 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]2[CH2:14][CH2:13][CH:12]([CH3:15])[CH2:11]2)=[CH:4][C:3]=1[N:16]1[C:20](=[O:21])[C:19]2[CH2:22][CH2:23][CH2:24][CH2:25][C:18]=2[C:17]1=[O:26].[CH2:27]([N:29](CC)CC)[CH3:28].[CH:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]2[CH2:14][CH2:13][CH:12]([CH3:15])[CH2:11]2)=[CH:4][C:3]=1[NH:16][C:17](=[O:26])[C:18]1[CH2:25][CH2:24][CH2:23][CH2:22][C:19]=1[C:20]([NH:29][CH:27]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:28])=[O:21]

Participants

4

Reactant 3

HCID 241BenzeneHCID 8471TriethylamineHCID 15279392HCID 15279392, compound

Product 1

HCID 19425286HCID 19425286, compoundYield 98.1%

Procedure

N-{2-Fluoro-4-chloro-5-(3-methylcyclopentyl)oxyphenyl)-3,4,5,6-tetrahydrophthalimide (1.00 g, 2.65 mmol), R-(+)-1-phenylethylamine (0.530 g, 4.37 mmol), triethylamine (0.340 g, 0.470 mmol) and benzene (25 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 precipitated crystals were isolated by filtration. The crystals were washed with hexane and dried to obtain N-{2-fluoro-4-chloro-5-(3-methylcyclopentyl)oxyphenyl}-N'-(1-phenylethyl)-3,4,5,6-tetrahydrophthalamide as white crystals (1.297 g, 98.1% yield).

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe precipitated crystals were isolated by filtration
  4. washThe crystals were washed with hexane
  5. customdried

Sources & evidence

ORD record
ord-c9ef151d21ce491d9ff92772a93db747
Source dataset
uspto-grants-1996_09
Patent number
US05554581

Reaction notes

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