Potassium Carbonate → 3-(R, S)-(1-Cyano-1,1-diphenylmethyl)-1-(4-carbamoylphenethyl)piperidine

HRID 21393

Reaction equation

HRID 21393 reaction equation
[C:1]([C:3]([CH:16]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)#[N:2].[C:22]([C:25]1[CH:33]=[CH:32][C:28]([CH2:29][CH2:30]Br)=[CH:27][CH:26]=1)(=[O:24])[NH2:23].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:3]([CH:16]1[CH2:21][CH2:20][CH2:19][N:18]([CH2:30][CH2:29][C:28]2[CH:32]=[CH:33][C:25]([C:22](=[O:24])[NH2:23])=[CH:26][CH:27]=2)[CH2:17]1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 136337463-(R,S)-(1-cyano-1,1-diphenylmethyl)piperidineHCID 220378844-Carbamoylphenethyl bromide

Product 1

HCID 212240843-(R, S)-(1-Cyano-1,1-diphenylmethyl)-1-(4-carbamoylphenethyl)piperidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 3-(R,S)-(1-cyano-1,1-diphenylmethyl)piperidine (0.303 g), 4-carbamoylphenethyl bromide (0.275 g--see Preparation 5), anhydrous potassium carbonate (0.4 g) and acetonitrile (10 ml) was heated under reflux for 5 hours. The mixture was concentrated in vacuo and the residue partitioned between dichloromethane (50 ml) and 10% aqueous potassium carbonate (50 ml). The layers were separated and the aqueous layer extracted with dichloromethane (3×20 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give a gum which was purified by column chromatography on silica eluting with dichloromethane containing methanol (5%). The product-containing fractions were combined and concentrated inn vacuo to give the title compound as a gum, yield 0.065 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue partitioned between dichloromethane (50 ml) and 10% aqueous potassium carbonate (50 ml)
  5. customThe layers were separated
  6. extractionthe aqueous layer extracted with dichloromethane (3×20 ml)
  7. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto give a gum which
  10. customwas purified by column chromatography on silica eluting with dichloromethane
  11. additioncontaining methanol (5%)
  12. concentrationconcentrated inn vacuo

Sources & evidence

ORD record
ord-f3d9887db70a4013b3e8df2ebd391a4f
Source dataset
uspto-grants-1995_06
Patent number
US05422358

Linked notes

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