Potassium Carbonate → HCID 53973189, compound

HRID 2106662Notes

Reaction equation

HRID 2106662 reaction equation
Br[CH2:2][CH2:3][CH:4]=[C:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1.[NH:18]1[CH2:28][CH2:27][CH2:26][CH:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:19]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:12]1([C:5]([C:6]2[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=2)=[CH:4][CH2:3][CH2:2][N:18]2[CH2:28][CH2:27][CH2:26][CH:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 98969Ethyl nipecotateHCID 53858518HCID 53858518, compound

Product 1

HCID 53973189HCID 53973189, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Bromo-4-phenyl-4-(4-pyridyl)but-3-ene (1.0 g, 3.5 mmol), ethyl nipecotate (0.72 g, 4.6 mmol) and potassium carbonate (1.93 g, 14.0 mmol) in acetone (30 ml) were stirred at room temperature for 5 days. The reaction mixture was filtered, and evaporated to a residue which was purified by flash chromatography on silica gel (Merck Art 9385). Elution with dichloromethane/ethanol/25% ammonium solution (190:9:1) provided the title compound as an oil. T.l.c. rf=0.23 (SiO2, CH2Cl2 /EtOH/NH3 (190:9:1)).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated to a residue which
  3. customwas purified by flash chromatography on silica gel (Merck Art 9385)
  4. washElution with dichloromethane/ethanol/25% ammonium solution (190:9:1)

Sources & evidence

ORD record
ord-45eae05b3db24fa78d41b004cea78fe2
Source dataset
uspto-grants-1990_06
Patent number
US04931450

Reaction notes

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