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

HRID 1720383Notes

Reaction equation

HRID 1720383 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:19](=[O:20])[C:18]2[CH2:21][CH2:22][CH2:23][CH2:24][C:17]=2[C:16]1=[O:25].[CH:26]([NH2:29])([CH3:28])[CH3:27]>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:16](=[O:25])[C:17]1[CH2:24][CH2:23][CH2:22][CH2:21][C:18]=1[C:19]([NH:29][CH:26]([CH3:28])[CH3:27])=[O:20]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 15279390N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydrophthalimide

Product 1

HCID 19425288N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-isopropyl-3,4,5,6-tetrahydrophthalamideYield 60.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-(2-Fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydrophthalimide (1.00 g, 2.75 mmol), isopropylamine (0.600 g, 10.2 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 precipitated crystals were isolated by filtration. The crystals were washed with hexane and dried to obtain N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-isopropyl-3,4,5,6-tetrahydrophthalamide as white crystals (0.700 g, 60.0% yield).

Workup

  1. customAfter completion of the reaction
  2. customthe precipitated crystals were isolated by filtration
  3. washThe crystals were washed with hexane
  4. customdried

Sources & evidence

ORD record
ord-3cb85ec636104bfb939d049618808519
Source dataset
uspto-grants-1996_04
Patent number
US05506190

Reaction notes

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