Sodium hydride → Tert-butyl 4-(3-phenyl-2-propenyloxy)piperidine-1-carboxylate

HRID 856061Notes

Reaction equation

HRID 856061 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].[CH2:17](Cl)[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C.C(OCC)(=O)C>[C:20]1([CH:19]=[CH:18][CH2:17][O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 94242Benzene, (3-chloro-1-propenyl)-HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 69479286Tert-butyl 4-(3-phenyl-2-propenyloxy)piperidine-1-carboxylateYield 50.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl 4-hydroxypiperidine-1-carboxylate (0.396 g, 1.97 mmol) was dissolved in DMF (5 ml), to which sodium hydride (0.086 g, 2.16 mmol) was added, and the mixture was stirred at room temperature for 1 hour. Cinnamyl chloride (0.300 g, 1.97 mmol) was added to the mixture while cooling in an ice-bath, and the resulting mixture was stirred overnight. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with water and brine. The organic layer was dried over magnesium sulfate, and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=6/1) to afford tert-butyl 4-(3-phenyl-2-propenyloxy)piperidine-1-carboxylate (0.314 g, yield 50%) as a yellow oil.

Workup

  1. additionwas added
  2. temperaturewhile cooling in an ice-bath
  3. stirringthe resulting mixture was stirred overnight
  4. washthe mixture was washed with water and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=6/1)

Sources & evidence

ORD record
ord-8e46c0d6e92f459d921422d93d927582
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

Loading…