Piperidine → HCID 68751051, compound

HRID 333330Notes

Reaction equation

HRID 333330 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1.[C:15]([CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])#[N:16].N1CCCCC1>CCO>[C:15](/[C:17](=[CH:11]/[C:10]1[CH:13]=[CH:14][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:8][CH:9]=1)/[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])#[N:16]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 70693tert-Butyl cyanoacetateHCID 15152404-Pyridin-2-ylbenzaldehyde

Product 1

HCID 68751051HCID 68751051, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
73 °C

Procedure

To a solution of 4-(pyridin-2-yl)-benzaldehyde (300 mg, 1.638 mmol) in EtOH (5 ml) at room temperature was added tert-butyl 2-cyanoacetate (0.281 ml, 1.965 mmol) followed by piperidine (0.016 ml, 0.164 mmol). The mixture was stirred at 73° C. overnight. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. To the obtained mixture was added water and then extracted with DCM. The combined organic layer was washed with brine and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by flash chromatography (silica gel, 15 to 30% EtOAc/Heptane) and gave the title compound: 350 mg (yield: 70%). LCMS (condition B): 307.2 (M+1); retention time=1.30 min.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionTo the obtained mixture was added water
  4. extractionextracted with DCM
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by flash chromatography (silica gel, 15 to 30% EtOAc/Heptane)

Sources & evidence

ORD record
ord-6b95348072a642e38b88d2be4449c864
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

Loading…