Potassium Carbonate → 2-[4-(Phenylethynyl)piperidin-1-yl]ethanamine

HRID 1444549Notes

Reaction equation

HRID 1444549 reaction equation
[C:1]1([C:7]#[C:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrCCC1C=CC=[C:20]2[C:21]([NH:23]C(=O)C=12)=O.C([O-])([O-])=O.[K+].[K+]>C(#N)C.C(OCC)(=O)C>[C:1]1([C:7]#[C:8][CH:9]2[CH2:10][CH2:11][N:12]([CH2:20][CH2:21][NH2:23])[CH2:13][CH2:14]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 179869654-(Phenylethynyl)piperidineHCID 219600212-Bromoethylphthalimide

Product 1

HCID 179869542-[4-(Phenylethynyl)piperidin-1-yl]ethanamine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(Phenylethynyl)piperidine (0.5 mmol, 92 mg) was dissolved in acetonitrile (anhydrous 4 Å, 4 mL) together with bromoethylphtalimide (0.5 mmol, 128 mg) and K2CO3 (2 mmol, 276 mg). The reaction mixture was heated to reflux for 3 hours, diluted with ethyl acetate (50 mL) and washed with HCl/aq (1M, 50 mL). The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The protection group was removed by stirring the compound in methylamine (33% in ethanol, 5 mL) for another 3 hours. The mixture was evaporated, diluted with ethyl acetate (50 mL) and washed with NaOH (1M, 50 mL). The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The crude product was used without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. washwashed with HCl/aq (1M, 50 mL)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe protection group was removed
  8. customThe mixture was evaporated
  9. additiondiluted with ethyl acetate (50 mL)
  10. washwashed with NaOH (1M, 50 mL)
  11. dry with materialThe organic phase was dried over Na2SO4
  12. filtrationfiltered
  13. customevaporated to dryness
  14. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-7ffb9968e0db4296bc25c2cbc40fdae0
Source dataset
uspto-grants-2010_02
Patent number
US07662845B2

Reaction notes

Loading…