Dimethylformamide → HCID 23150285, compound

HRID 657626Notes

Reaction equation

HRID 657626 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.CN(C)C=O.Cl[CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([CH:29]2[CH2:34][CH2:33][C:32](=[O:35])[CH2:31][CH2:30]2)=[CH:25][CH:24]=1>>[O:35]=[C:32]1[CH2:33][CH2:34][CH:29]([C:26]2[CH:25]=[CH:24][C:23]([O:22][CH2:21][CH2:20][CH2:19][N:7]3[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]3)=[CH:28][CH:27]=2)[CH2:30][CH2:31]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 23150298HCID 23150298, compound

Product 1

HCID 23150285HCID 23150285, compound

Procedure

A suspension of potassium carbonate (3.11 g) in a mixture of 4-[4-(3-chloropropoxy)phenyl]cyclohexanone (2 g), piperidine (2.22 mL) and N,N-dimethylformamide (40 mL) is heated for three hour at a temperature close to 110° C., then stirred for twenty hour at room temperature. The mixture is concentrated under reduced pressure and dissolved in ethyl acetate (150 mL) and water (150 mL). The organic phase is washed twice with water (100 mL), dried over magnesium sulphate, concentrated under reduced pressure and purified by chromatography over silica gel with a gradient dichloromethane/methanol from 95/5 to 90/10. Fractions containing the product are pooled and concentrated under reduced pressure affording 1.94 g of 1-{3-[4-(4-oxocyclohexyl)phenoxy]propyl}-piperidine as a yellow solid used without further purification.

Workup

  1. temperatureis heated for three hour at a temperature
  2. customclose to 110° C.
  3. concentrationThe mixture is concentrated under reduced pressure
  4. dissolutiondissolved in ethyl acetate (150 mL)
  5. washThe organic phase is washed twice with water (100 mL)
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. custompurified by chromatography over silica gel with a gradient dichloromethane/methanol from 95/5 to 90/10
  9. additionFractions containing the product
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cac5c24061aa42f098675aee61b3ca05
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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