Acetic Acid → 1-Benzyl-4-phenyl-1,2,3,6-tetrahydropyridine

HRID 276902Notes

Reaction equation

HRID 276902 reaction equation
[C:1]1([C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O)(=O)C.C(OCC)(=O)C>ClC(Cl)C>[CH2:13]([N:10]1[CH2:9][CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 8857Ethyl AcetateHCID 825531,2,3,6-Tetrahydro-4-phenylpyridine

Product 1

HCID 5636091-Benzyl-4-phenyl-1,2,3,6-tetrahydropyridineYield 50%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

1,2,3,6-Tetrahydro-4-phenylpyridine (410 mg, 2.6 mmol), benzaldehyde (300 mg, 2.9 mmol), sodium triacetoxyborate (1.1 g, 5.2 mmol) and acetic acid (1.5 ml, 26 mmol) were stirred in dichloroethane at a room temperature for 14 hours. To the reaction solution was added ethyl acetate, and the resulting solution was washed with sodium hydroxide aqueous solution (1 N) and saturated brine and dried with anhydrous sodium sulfate. Then the solvent was evaporated under a reduced pressure. Thereafter, the resulting residue was separated and purified by a silica gel column chromatography to obtain 330 mg of the title compound (1.3 mmol, 45% in yield).

Workup

  1. washthe resulting solution was washed with sodium hydroxide aqueous solution (1 N) and saturated brine
  2. dry with materialdried with anhydrous sodium sulfate
  3. customThen the solvent was evaporated under a reduced pressure
  4. customThereafter, the resulting residue was separated
  5. custompurified by a silica gel column chromatography

Sources & evidence

ORD record
ord-d9ca1c3daf274125b95fbf68b4162893
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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