Piperazine → 1-[6-(Trifluoromethyl)pyridin-2-yl]piperazine

HRID 1436795Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[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:4]1[N:3]=[C:2]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 2-chloro-6-(trifluoromethyl)pyridine (1.0 g, 5.5 mmol), piperazine (1.4 g, 16.0 mmol), and triethylamine (1.5 mL, 11.0 mmol) were mixed in DMF (10 mL) in a sealed tube. The mixture was heated at 100° C. overnight. The reaction mixture was concentrated and chromatographed on silica gel (ethyl acetate to EA/MeOH/Bt3N=9:1:0.5) to give 1.05g of the desired product. MS calculated for C10H12F3N3:(M+H) 232.1; found 232.1.

Workup

concentrationThe reaction mixture was concentrated
customchromatographed on silica gel (ethyl acetate to EA/MeOH/Bt3N=9:1:0.5)

Sources & evidence

ORD record: ord-7bdc5eebaa184594ab71b6f8017c98dc
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618970B2

Reaction notes

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