Cesium carbonate → HCID 59599441, compound

HRID 2266689Notes

Reaction equation

HRID 2266689 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>CN(C)C=O>[Br:1][C:2]1[N:3]=[CH:4][N:5]([CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH:6]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 178418934HCID 178418934, compound

Product 1

HCID 59599441HCID 59599441, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-bromo-imidazole (217 mg, 1.48 mmol) and cesium carbonate (875 mg, 2.69 mmol) in dimethylformamide (5 mL) was stirred for 30 minutes. 4-(2-Chloro-ethyl)-morpholine hydrochloride (250 mg, 1.34 mmol) was added and the mixture was heated to 50° C. After heating overnight the reaction was concentrated by rotary evaporation. The residue was suspended in a mixture of dichloromethane and methanol and filtered. The filtrate was concentrated by rotary evaporation. The residue was purified by silica gel chromatography using gradient elution of dichloromethane, methanol to afford 4-[2-(4-Bromo-imidazol-1-yl)-ethyl]-morpholine (148 mg, 42%).

Workup

  1. temperatureAfter heating overnight the reaction
  2. concentrationwas concentrated by rotary evaporation
  3. additionThe residue was suspended in a mixture of dichloromethane and methanol
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated by rotary evaporation
  6. customThe residue was purified by silica gel chromatography
  7. washelution of dichloromethane, methanol

Sources & evidence

ORD record
ord-328321938cec4472abbd2868edfe20a5
Source dataset
uspto-grants-2010_12
Patent number
US07858643B2

Reaction notes

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