Phenethyl bromide → HCID 13536280, compound

HRID 1380326Notes

Reaction equation

HRID 1380326 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]([NH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)=[O:12].[C:20]1([CH2:26][CH2:27]Br)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]([NH:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:27][CH2:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)=[O:12]

Participants

6

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 13752627HCID 13752627, compound

Product 1

HCID 13536280HCID 13536280, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.6 g of 5-fluoro-N-(4-piperidyl)indole-3-carboxamide in a mixture of 50 ml of toluene and 10 ml of dimethylformamide were added 0.43 g of 2-phenylethylbromide and 1 g of potassium carbonate, and the whole mixture was stirred while heating and refluxing for 7 hours. After cooling, to the reaction mixture was added 50 ml of ice-cold water and stirred for 1 hour. The precipitated crystals were filtered, and washed with water and ethyl acetate. An organic layer was separated from the filtrate, dried over magnesium sufate and concentrated under reduced pressure. The residue was treated with a small amount of ethyl acetate to crystallize, and the crystals were filtered and combined with the crystals obtained as above. All of the crystals were recrystallized from methanol to give 5-fluoro-N-[1-(2-phenylethyl)-4-piperidyl]indole-3-carboxamide, melting at 238°-240° C.

Workup

  1. temperaturewhile heating
  2. temperaturerefluxing for 7 hours
  3. temperatureAfter cooling, to the reaction mixture
  4. stirringstirred for 1 hour
  5. filtrationThe precipitated crystals were filtered
  6. washwashed with water and ethyl acetate
  7. customAn organic layer was separated from the filtrate
  8. dry with materialdried over magnesium sufate
  9. concentrationconcentrated under reduced pressure
  10. additionThe residue was treated with a small amount of ethyl acetate
  11. customto crystallize
  12. filtrationthe crystals were filtered
  13. customobtained as above
  14. customAll of the crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-b77d4e393e1e4bc4915c878819495dcf
Source dataset
uspto-grants-1986_04
Patent number
US04581355

Reaction notes

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