Water → Ethyl 4-[1-benzyl-1,2,3,6-tetrahydropyrid-4-yl]benzoate

HRID 1059323Notes

Reaction equation

HRID 1059323 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:12][CH:13]=2)=[CH:4][CH:3]=1.C([Li])CCC.[C:26](=O)([O:30]CC)[O:27][CH2:28][CH3:29].O>O1CCCC1.CCCCCC>[CH2:14]([N:11]1[CH2:12][CH:13]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:26]([O:27][CH2:28][CH3:29])=[O:30])=[CH:3][CH:4]=2)[CH2:9][CH2:10]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7766Diethyl CarbonateHCID 112443314-(4-Bromophenyl)-1,2,3,6-tetrahydro-1-(phenylmethyl)pyridineHCID 178418339Butyllithium

Product 1

HCID 11450082Ethyl 4-[1-benzyl-1,2,3,6-tetrahydropyrid-4-yl]benzoate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 11 g of 4-(4-bromophenyl)-1-benzyl-1,2,3,6-tetrahydropyridine in 200 ml of tetrahydrofuran was added 27 ml of a 2.5 M solution of n-butyllithium in hexane at −78° C. and the resulting mixture was stirred at the same temperature for 15 minutes. Into the reaction mixture was dropped 42 ml of diethyl carbonate and the mixture was heated to room temperature over 15 minutes. After adding water, the reaction mixture was extracted with ethyl acetate, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 2.8 g of the title compound as a yellow oily substance.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a35b3606e33445a8b769d15d115beedf
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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