Trifluoroacetic acid → 1',2',3',6'-Tetrahydro-2,4'-bipyridine

HRID 1403617Notes

Reaction equation

HRID 1403617 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH:8]=1.FC(F)(F)C(O)=O>ClCCl>[NH:10]1[CH2:9][CH:8]=[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 16094711tert-Butyl 5',6'-dihydro-[2,4'-bipyridine]-1'(2'H)-carboxylate

Product 1

HCID 151668421',2',3',6'-Tetrahydro-2,4'-bipyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.1 g, 4.23 mmol) in dichloromethane (50 ml) was added trifluoroacetic acid (4 ml), and the reaction mixture was allowed to react with stirring overnight at room temperature. The reaction mixture was concentrated in vacuo to afford 2-(1,2,3,6-tetrahydropyridin-4-yl)pyridine as a crude yellow oil (600 mg).

Workup

  1. customto react
  2. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-85b7448ed18f4e56b733957e4e753b0d
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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