Sodium Bicarbonate → 2-[4-(4-Trifluoromethylphenyl)piperazin-1-yl]methyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole

HRID 856279Notes

Reaction equation

HRID 856279 reaction equation
Cl[C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[CH3:10][C:11]1([CH2:14][N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)[CH2:13][O:12]1.C(=O)([O-])O.[Na+]>C(O)CC>[F:30][C:27]([F:28])([F:29])[C:24]1[CH:23]=[CH:22][C:21]([N:18]2[CH2:17][CH2:16][N:15]([CH2:14][C:11]3([CH3:10])[O:12][C:2]4=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]4[CH2:13]3)[CH2:20][CH2:19]2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 230815381-(2-Methyl-2-oxiranylmethyl)-4-(4-trifluoromethylphenyl)piperazineHCID 178526855HCID 178526855, compound

Product 1

HCID 103415552-[4-(4-Trifluoromethylphenyl)piperazin-1-yl]methyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazoleYield 30.2%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

To a solution of 2-chloro-4-nitro-1H-imidazole (1.59 g, 10.8 mmol) and 1-(2-methyloxiran-2-ylmethyl)-4-(4-trifluoromethylphenyl)piperazine (3.23 g, 10.8 mmol) in 1-propanol (20 ml), sodium hydrogencarbonate (1.95 g, 23.8 mmol) was added followed by stirring under reflux overnight. The reaction mixture was concentrated under reduced pressure. The residue was added water, and the solution was extracted with methylene chloride. The organic phase was dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1) and crystallized from methylene chloride-isopropyl ether to afford 2-[4-(4-trifluoromethylphenyl)piperazin-1-yl]methyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole (1.34 g, yield 29%) as a a light yellow powder.

Workup

  1. temperatureunder reflux overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was added water
  4. extractionthe solution was extracted with methylene chloride
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1)
  9. customcrystallized from methylene chloride-isopropyl ether

Sources & evidence

ORD record
ord-41a7f8589a42425f9f35d1d43065d48a
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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