Potassium Carbonate → 1-Diphenylmethylpiperidin-3-carboxamide

HRID 362906Notes

Reaction equation

HRID 362906 reaction equation
Br[CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH:15]1[CH2:23][CH2:22][CH2:21][CH:17]([C:18]([NH2:20])=[O:19])[CH2:16]1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.CC#N>[C:3]1([CH:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:15]2[CH2:23][CH2:22][CH2:21][CH:17]([C:18]([NH2:20])=[O:19])[CH2:16]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 929803-PiperidinecarboxamideHCID 236603Bromodiphenylmethane

Product 1

HCID 541420131-Diphenylmethylpiperidin-3-carboxamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Step 1): A solution of bromodiphenylmethane (48.2 g, 195 mmol) in DMSO (30 ml) was added dropwise to a solution of nipecotamide (25 g, 195 mmol) and K2CO3 (27 g, 195 mmol) in CH3CN (100 ml) and DMSO (50 ml) under stirring and cooling in an ice-bath for 1 hour. After the addition was complete, the mixture was stirred overnight at room temperature. The insoluble precipitates were filtered off and then the filtrate was evaporated. To the residue was added H2O and AcOEt, and agitated. The organic layer was washed with H2O, dried over MgSO4 and evaporated to give 1-diphenylmethylpiperidin-3-carboxamide, 33 g (57.5%): mp 86°-87° C.

Workup

  1. temperaturecooling in an ice-bath for 1 hour
  2. additionAfter the addition
  3. stirringthe mixture was stirred overnight at room temperature
  4. customThe insoluble precipitates
  5. filtrationwere filtered off
  6. customthe filtrate was evaporated
  7. additionTo the residue was added H2O and AcOEt
  8. stirringagitated
  9. washThe organic layer was washed with H2O
  10. dry with materialdried over MgSO4
  11. customevaporated

Sources & evidence

ORD record
ord-be337de1b1894706a9ccc89100f9c11e
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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