Dimethylcarbamoyl Chloride → HCID 69677555, compound

HRID 1017683Notes

Reaction equation

HRID 1017683 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+].[CH3:30][N:31]([CH3:35])[C:32]([Cl:34])=[O:33]>C(#N)C.ClCCl.C(OCC)(=O)C>[ClH:34].[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:32](=[O:33])[N:31]([CH3:35])[CH3:30]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 10796Cesium carbonateHCID 18403905HCID 18403905, compound

Product 1

HCID 69677555HCID 69677555, compoundYield 73%

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 (1.0 g) and cesium carbonate (1.0 g) in 25% acetonitrile/dichloromethane was added dimethylcarbamyl chloride (0.7 g), and the reaction mixture was stirred for 18 hrs, under nitrogen. The reaction mixture was diluted with ethyl acetate, and washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was flash chromatographed (silica) eluting with 2% methanol/dichloromethane. The appropriate fractions were collected and concentrated. The residue was dissolved in ethyl acetate and ethereal hydrogen chloride was added. The precipitate was collected to give product 0.9 g (73%), mp 192-193° C.

Workup

  1. washwashed with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customchromatographed (silica)
  5. washeluting with 2% methanol/dichloromethane
  6. customThe appropriate fractions were collected
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in ethyl acetate
  9. additionethereal hydrogen chloride was added
  10. customThe precipitate was collected

Sources & evidence

ORD record
ord-80938551bd3a4f71a1d26060724ea38b
Source dataset
uspto-grants-2002_11
Patent number
US06479495B1

Reaction notes

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