Piperazine → 1-[6-Methyl-4-(trifluoromethyl)pyridin-2-yl]piperazine

HRID 1436801Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([CH3:12])[N:3]=1.[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(N(CC)CC)C>O1CCOCC1.O>[CH3:12][C:4]1[N:3]=[C:2]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 2-chloro-6-methyl-4-(trifluoromethyl)pyridine (1.0 g, 5.11 mmol), piperazine (1.32 g, 15.3 mmol), and triethylamine (0.71 mL, 5.1 mmol) were mixed in 1,4-dioxane (10 mL). After stirring at 100° C. for 5 h, the reaction solution was diluted with water and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography (10%MeOH/5%Et3N/EtOAc) to yield the desired product (880 mg, 70.2%). LCMS calculated for C11H15F3N3:(M+H) 246.1; found 246.1.

Workup

extractionextracted with ethyl acetate three times
dry with materialdried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude residue was purified by flash column chromatography (10%MeOH/5%Et3N/EtOAc)

Sources & evidence

ORD record: ord-cf3645045d9b405f97ffd0f6e5a13a8d
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618970B2

Reaction notes

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