Cesium carbonate → HCID 69677511, compound

HRID 1017684Notes

Reaction equation

HRID 1017684 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:13][CH2:12]2)[CH:6]=[CH:5][C:4]=1[OH:23].C(=O)([O-])[O-].[Cs+].[Cs+].[N:30]1([C:36]([Cl:38])=[O:37])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>C(#N)C.ClCCl.C(OCC)(=O)C>[ClH:38].[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:15][CH2:16]2)[CH:6]=[CH:5][C:4]=1[O:23][C:36]([N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)=[O:37]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 848104-Morpholinecarbonyl chlorideHCID 18403905HCID 18403905, compound

Product 1

HCID 69677511HCID 69677511, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

To a solution of 2-methoxy-4-[2-(4-pyridin-2-yl-piperazin-1-yl)ethyl)phenol (1.5 g) and cesium carbonate (1.6 g) in 25% acetonitrile/dichloromethane was added 4-morpholinecarbonyl chloride (1.4 g), with stirring, under nitrogen. The reaction mixture was stirred for 18 hrs under nitrogen, diluted with ethyl acetate, and the layers were separated. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was flash chromatographed (silica), eluting with 2% methanoludichloromethane. The appropriate fractions were collected and concentrated. The residue was dissolved in ethyl acetate and ethereal hydrochloride was added. The precipitate was collected and recrystallized from ethyl ethanol/ether to give 0.9 g (75%) of product, mp 185-186° C.

Workup

  1. stirringThe reaction mixture was stirred for 18 hrs under nitrogen
  2. customthe layers were separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customchromatographed (silica)
  7. washeluting with 2% methanoludichloromethane
  8. customThe appropriate fractions were collected
  9. concentrationconcentrated
  10. dissolutionThe residue was dissolved in ethyl acetate
  11. additionethereal hydrochloride was added
  12. customThe precipitate was collected
  13. customrecrystallized from ethyl ethanol/ether

Sources & evidence

ORD record
ord-8724e466a645458c99019d71ce7ecba0
Source dataset
uspto-grants-2002_11
Patent number
US06479495B1

Reaction notes

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