4-[3-(Trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine → 1-(3-Pyridylacetyl)-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine

HRID 1248014Notes

Reaction equation

HRID 1248014 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]([O:10]C2C=CC([N+]([O-])=O)=CC=2)=O)[CH:2]=1.[F:20][C:21]([F:35])([F:34])[C:22]1[CH:23]=[C:24]([C:28]2[CH2:29][CH2:30][NH:31][CH2:32][CH:33]=2)[CH:25]=[CH:26][CH:27]=1>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]([N:31]2[CH2:30][CH:29]=[C:28]([C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([C:21]([F:20])([F:34])[F:35])[CH:23]=3)[CH2:33][CH2:32]2)=[O:10])[CH:2]=1

Participants

4

Reactant 2

HCID 111280344-[3-(Trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridineHCID 20280550p-Nitrophenyl 3-pyridylacetate

Product 1

HCID 202805321-(3-Pyridylacetyl)-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridineYield 52.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 11.3 g of p-nitrophenyl 3-pyridylacetate and 10 g of 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine in 150 ml of ethanol is stirred 1 hour at room temperature, then concentrated under reduced pressure. The residue is dissolved in diethyl ether, the solution is washed with water, then with sodium hydroxide and again with water, dried on anhydrous sodium sulfate and concentrated. Thus, 1-(3-pyridylacetyl)-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine (8 g) is obtained as an oil which is used for the subsequent reaction.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue is dissolved in diethyl ether
  3. washthe solution is washed with water
  4. dry with materialwith sodium hydroxide and again with water, dried on anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f7a8c886b30c4963a05c64b547a0290b
Source dataset
uspto-grants-1985_06
Patent number
US04521428

Reaction notes

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