Benzene → N-(2-fluoro-4-chloro-5-cyclohexyloxyphenyl)-N'-(1-phenylethyl)-3,4,5,6-tetrahydrophthalamide

HRID 1720400Notes

Reaction equation

HRID 1720400 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][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[CH2:15][CH2:14][CH2:13][CH2:12][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 13604754N-(2-Fluoro-4-chloro-5-cyclohexyloxyphenyl)-3,4,5,6-tetrahydrophthalimide

Product 1

HCID 19425208N-(2-fluoro-4-chloro-5-cyclohexyloxyphenyl)-N'-(1-phenylethyl)-3,4,5,6-tetrahydrophthalamideYield 82.3%

Procedure

N-(2-Fluoro-4-chloro-5-cyclohexyloxyphenyl)-3,4,5,6-tetrahydrophthalimide (1.00 g, 2.65 mmol), R-(+)-1-phenylethylamine (0.65 g, 5.36 mmol), triethylamine (0.268 g, 2.65 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-cyclohexyloxyphenyl)-N'-(1-phenylethyl)-3,4,5,6-tetrahydrophthalamide as white crystals (1.09 g, 82.3% 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-36a05af1312c45e0bb0553b8bc4bdd14
Source dataset
uspto-grants-1996_04
Patent number
US05506190

Reaction notes

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