Piperazine → 1-[4-(Trifluoromethyl)pyridin-2-yl]piperazine

HRID 1436759Notes

Reaction equation

HRID 1436759 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(N(CC)CC)C>CN(C=O)C>[F:9][C:8]([F:11])([F:10])[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:7]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 8471TriethylamineHCID 1449582-Chloro-4-(trifluoromethyl)pyridine

Product 1

HCID 112184921-[4-(Trifluoromethyl)pyridin-2-yl]piperazineYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-4-(trifluoromethyl)pyridine (2.0 g, 11 mmol), piperazine (3 g, 30 mmol) and triethylamine (3.1 mL, 22 mmol) in DMF (10 mL) was heated at 100° C. overnight and concentrated in vacuo. The residue was purified by column chromatography on silica gel (EtOAc to EtOAc/MeOH/Et3N=9/1/0.5) to give 1.09g (43%) of pure product. MS calculated for C10H12F3N3: (M+H) 232; found 232.1.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography on silica gel (EtOAc to EtOAc/MeOH/Et3N=9/1/0.5)

Sources & evidence

ORD record
ord-4ef9c36f56fd43839984728a74d5569c
Source dataset
uspto-grants-2009_11
Patent number
US07618970B2

Reaction notes

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