Cesium carbonate → Enerisant

HRID 1364215Notes

Reaction equation

HRID 1364215 reaction equation
I[C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][C@H:11]2[CH3:15])=[CH:4][CH:3]=1.[NH:18]1[CH:22]=[C:21]([C:23]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[O:24])[CH:20]=[N:19]1.CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O.[Cu](I)I>[CH3:15][C@@H:11]1[CH2:12][CH2:13][CH2:14][N:10]1[CH2:9][CH2:8][CH2:7][O:6][C:5]1[CH:16]=[CH:17][C:2]([N:18]2[CH:22]=[C:21]([C:23]([N:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)=[O:24])[CH:20]=[N:19]2)=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 20784942Morpholino(1H-pyrazol-4-yl)methanoneHCID 57675747(2R)-1-[3-(4-iodophenoxy)propyl]-2-methylpyrrolidine

Product 1

HCID 42601503Enerisant

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of (2R)-1-[3-(4-iodophenoxy)propyl]-2-methylpyrrolidine obtained in Example 1-(2) (0.30 g), 4-(1H-pyrazol-4-ylcarbonyl)morpholine obtained in Example 6-(1) (0.19 g), (rac-trans-N,N′-dimethylcyclohexane-1,2-diamine (0.049 g), copper iodide (0.017 g) and cesium carbonate (0.57 g) in N,N-dimethylformamide (0.5 mL) was stirred at 120° C. for 1.5 hours. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=2:1 to 1:1). The resulting crystal was washed with isopropyl ether to give the titled compound (0.20 g) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=2:1 to 1:1)
  4. washThe resulting crystal was washed with isopropyl ether

Sources & evidence

ORD record
ord-223ee487499d4ddeb351b86285a75abb
Source dataset
uspto-grants-2011_02
Patent number
US07888354B2

Reaction notes

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