Potassium Carbonate → HCID 18947311, compound

HRID 1033038Notes

Reaction equation

HRID 1033038 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH2:17][CH2:18][NH:19][C:20]([CH:22]1[CH2:24][CH2:23]1)=[O:21].Br[CH:26]1[CH2:31][CH2:30][CH2:29][CH:28]=[CH:27]1>CC(C)=O>[CH:26]1[CH2:31][CH2:30][CH2:29][CH:28]([O:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH:12]=[C:11]3[CH2:17][CH2:18][NH:19][C:20]([CH:22]2[CH2:24][CH2:23]2)=[O:21])[CH:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1370573-BromocyclohexeneHCID 18947274HCID 18947274, compound

Product 1

HCID 18947311HCID 18947311, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.98×10-2 mol of potassium carbonate, 1.33×10-2 mol of N-[2-(5-hydroxyindol-3-yl)ethyl]cyclopropylcarboxamide dissolved in 20 cm3 of anhydrous acetone, and 2.1×10-2 mol of 3-bromocyclohexene are introduced into a 50 cm3 flask with a ground neck. The mixture is heated under reflux for 22 hours. The reaction medium is filtered and the filtrate is evaporated under reduced pressure Recrystallisation of the evaporation residue in ethyl acetate yields purified N-{2-[5-(cyclohexen-3-yloxy)indol-3-yl]ethyl}-cyclopropylcarboxamide.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 22 hours
  3. filtrationThe reaction medium is filtered
  4. customthe filtrate is evaporated under reduced pressure Recrystallisation of the evaporation residue in ethyl acetate
  5. customyields
  6. custompurified N-{2-[5-(cyclohexen-3-yloxy)indol-3-yl]ethyl}-cyclopropylcarboxamide

Sources & evidence

ORD record
ord-3deca8d2fa4b4be0ae757dfbc96b07b5
Source dataset
uspto-grants-1994_05
Patent number
US05308866

Reaction notes

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