Potassium Carbonate → HCID 21997548, compound

HRID 1977283Notes

Reaction equation

HRID 1977283 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:28][C@H:29]1[O:34][C@@H:33]([CH3:35])[CH2:32][NH:31][CH2:30]1>CN(C)C=O.C(OCC)(=O)C>[CH3:35][CH:33]1[CH2:32][N:31]([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=3)=[CH:8][CH:7]=2)[CH2:30][CH:29]([CH3:28])[O:34]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6415002,6-Dimethylmorpholine, cis-HCID 21997455HCID 21997455, compound

Product 1

HCID 21997548HCID 21997548, compoundYield 45.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 4-[4′-(3-bromopropyoxy)phenyl]benzoate (1.5 g), potassium carbonate (1.2 g) and cis-2,6-dimethylmorpholine (990.6 mg) in N,N-dimethyformamide was stirred for 15 hours at room temperature, then diluted with ethyl acetate and washed with water (5x), dried over magnesium sulfate, evaporated, then purified by silica gel chromatography (20:1 dichloromethane-ethanol elution) to give methyl 4-[4′-[3-(2,6-dimethylmorpholino)propoxy]phenyl]benzoate (755 mg).

Workup

  1. washwashed with water (5x)
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. custompurified by silica gel chromatography (20:1 dichloromethane-ethanol elution)

Sources & evidence

ORD record
ord-5436a3a7535b441e8e55c394fb6837f4
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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