Dicyclohexylcarbodiimide → 1-Isopropyl-4-[4-(9-fluorenylidene acetyloxy)benzoyl]piperazine

HRID 1198952Notes

Reaction equation

HRID 1198952 reaction equation
[CH:1]1[C:13]2[C:12](=[CH:14][C:15]([OH:17])=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.O[C:19]1[CH:35]=[CH:34][C:22]([C:23]([N:25]2[CH2:30][CH2:29][N:28]([CH:31]([CH3:33])[CH3:32])[CH2:27][CH2:26]2)=[O:24])=[CH:21][CH:20]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[CH:31]([N:28]1[CH2:29][CH2:30][N:25]([C:23](=[O:24])[C:22]2[CH:21]=[CH:20][C:19]([O:16][C:15](=[O:17])[CH:14]=[C:12]3[C:13]4[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=4[C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)=[CH:35][CH:34]=2)[CH2:26][CH2:27]1)([CH3:33])[CH3:32]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 967929H-Fluoren-9-ylideneacetic acidHCID 4740443Piperazine, 1-(4-hydroxybenzoyl)-4-(1-methylethyl)-

Product 1

HCID 157039881-Isopropyl-4-[4-(9-fluorenylidene acetyloxy)benzoyl]piperazine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a 20 ml chloroform solution containing 2.67 g (12 mmol) of 9-fluorenylidene acetic acid, 2.48 g (10 mmol) of 1-(4-hydroxybenzoyl)-4-isopropylpiperazine and 122 mg (1 mmol) of 4-dimethylaminopyridine was added 2.48 g (12 mmol) of dicyclohexyl carbodiimide, and the mixture was stirred at room temperature for 3 hours. Any insoluble matter which had formed was removed by filtration, and the filtrate was concentrated under reduced pressure. Thereafter, any insoluble matter was removed by filtration using 20 ml of ethyl acetate, and the filtrate was extracted up to 60 ml of 1N hydrochloric acid. After being washed with ethyl acetate, the extract was neutralized with sodium hydrogen carbonate and extracted up to 60 ml of chloroform. After being washed twice with water, the extract was dried over magnesium sulfate and concentrated under reduced pressure to obtain yellow crystals. Recrystallization of the crystals from ethyl acetate-petroleum ether gave yellow prismatic crystals.

Workup

  1. customAny insoluble matter which had formed
  2. customwas removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThereafter, any insoluble matter was removed by filtration
  5. extractionthe filtrate was extracted up to 60 ml of 1N hydrochloric acid
  6. washAfter being washed with ethyl acetate
  7. extractionextracted up to 60 ml of chloroform
  8. washAfter being washed twice with water
  9. dry with materialthe extract was dried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customto obtain yellow crystals
  12. customRecrystallization of the crystals from ethyl acetate-petroleum ether
  13. customgave yellow prismatic crystals

Sources & evidence

ORD record
ord-7e4bd91f25ca4f4eb2d403968a35945d
Source dataset
uspto-grants-1990_02
Patent number
US04898876

Reaction notes

Loading…