Cycloheptylamine → 2-Cycloheptylcarbamoylmethylfluorene

HRID 256624Notes

Reaction equation

HRID 256624 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:14][C:15](O)=[O:16].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[CH:43]1([NH2:50])[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1>CN(C)C=O>[CH:43]1([NH:50][C:15](=[O:16])[CH2:14][C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH2:12][C:13]=3[CH:1]=2)[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1

Participants

6

Reactant 4

HCID 2899CycloheptylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 232711852-(9H-fluoren-2-yl)acetic acid

Product 1

HCID 199361232-CycloheptylcarbamoylmethylfluoreneYield 65.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In dimethylformamide (50 ml) was dissolved 2-fluoreneacetic acid (2.24 g) followed by addition of 1-hydroxybenztriazole (2.0 g) and, then, dicyclohexylcarbodiimide (3.1 g) with constant stirring and ice-cooling. The mixture was further stirred at room temperature for 15 minutes. Cycloheptylamine (1.7 g) was then added under ice-cooling and the mixture was stirred at room temperature for 8 hrs. The resulting solid was filtered off and the filtrate was distilled under reduced pressure. The residue was extracted with 50 ml of chloroform and the extract was washed with 1N aqueous sodium hydroxide solution, 1N hydrochloric acid and water in the order mentioned and dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel column chromatography to give 2.1 g of N-cycloheptyl-2-fluoreneacetamide as a solid.

Workup

  1. temperatureice-cooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 8 hrs
  4. filtrationThe resulting solid was filtered off
  5. distillationthe filtrate was distilled under reduced pressure
  6. extractionThe residue was extracted with 50 ml of chloroform
  7. washthe extract was washed with 1N aqueous sodium hydroxide solution, 1N hydrochloric acid and water in the order
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was then distilled off under reduced pressure
  10. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7c7ebfdebacf4e4ba72b67bee50bba15
Source dataset
uspto-grants-1993_11
Patent number
US05258405

Reaction notes

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