Cesium carbonate → HCID 68689149, compound

HRID 1157805Notes

Reaction equation

HRID 1157805 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br.Br[CH2:22][C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1)=[O:24]>CN(C=O)C.O.C(OCC)(=O)C>[O:24]=[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1)[CH2:22][N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27762312-Bromo-1-(2-pyridinyl)-1-ethanone hydrobromide

Product 1

HCID 68689149HCID 68689149, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

Part A: To a mixture of tert-butyl piperazine-1-carboxylate (1.863 g, 10.00 mmol) and cesium carbonate (6.52 g, 20.00 mmol) in 50 mL of DMF at 25° C. was added 2-(bromoacetyl)pyridine hydrobromide (2.81 g, 10.00 mmol) in portions over five minutes. The reaction mixture then was stirred at 25° C. for 3 h. The resulting mixture was diluted with water and ethyl acetate. The phases were separated, and the organic phase was washed with water (×3) and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Column chromatography on silica gel (elution: 10-50% ethyl acetate/chloroform) provided 1.61 g (53%) of tert-butyl 4-(2-oxo-2-(pyridin-2-yl)ethyl)piperazine-1-carboxylate as a crystalline solid; 1H NMR (500 MHz, CDCl3) δ 8.63 (d, 1H, J=4.5 Hz), 8.05 (m, 1H), 7.85 (t, 1H, J=9 Hz), 7.49 (m, 1H), 4.30 (s, 2H), 3.62 (m, 4H), 2.75 (m, 4H), 1.46 (s, 9H).

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with water (×3) and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-111d649b36dc4c87bdac40fe32e1980f
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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