Water → (S)-[4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridin-1-yl]-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]methanone

HRID 856333Notes

Reaction equation

HRID 856333 reaction equation
Cl.Cl.[CH3:3][C@@:4]1([CH2:15][N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[O:8][C:7]2=[N:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][N:6]2[CH2:5]1.C(=O)([O-])[O-].[K+].[K+].[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH2:36][CH2:37][N:38]([C:41](Cl)=[O:42])[CH2:39][CH:40]=2)=[CH:31][CH:30]=1.O>CN(C=O)C>[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH2:40][CH2:39][N:38]([C:41]([N:19]3[CH2:18][CH2:17][N:16]([CH2:15][C@:4]4([CH3:3])[O:8][C:7]5=[N:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][N:6]5[CH2:5]4)[CH2:21][CH2:20]3)=[O:42])[CH2:37][CH:36]=2)=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 230816374-(4-Chlorophenyl)-1,2,3,6-tetrahydropyridine-1-carbonylchlorideHCID 69481767(S)-2-methyl-6-nitro-2-(piperazin-1-ylmethyl)-2,3-dihydroimidazo[2,1-b]oxazole dihydrochloride

Product 1

HCID 69479749(S)-[4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridin-1-yl]-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]methanoneYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of (S)-2-methyl-6-nitro-2-(piperazin-1-ylmethyl)-2,3-dihydroimidazo[2,1-b]oxazole dihydrochloride prepared in Example 408 (401 mg, 1.5 mmol), DMF (8 ml) and potassium carbonate (750 mg, 5.4 mmol) was stirred at room temperature for 10 minutes. To the reaction mixture, a solution of 4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridine-1-carbonylchloride (400 mg, 1.56 mmol) in DMF (3 ml) was added slowly with cooling on ice-bath followed by stirring at room temperature overnight. To the reaction mixture, water was added, and the solution was extracted with ethyl acetate. The organic phase was washed with water three times and a saturated saline solution, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was recrystallized from ethanol to afford (S)-[4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridin-1-yl]-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]methanone (380 mg, yield 53%) as a light yellow powder.

Workup

  1. temperaturewith cooling on ice-bath
  2. stirringby stirring at room temperature overnight
  3. extractionthe solution was extracted with ethyl acetate
  4. washThe organic phase was washed with water three times
  5. dry with materiala saturated saline solution, dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-2bbc24c329f74077b6aca330a70233e5
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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