Morpholine → HCID 66584430, compound

HRID 538013Notes

Reaction equation

HRID 538013 reaction equation
S(O[CH2:12][CH2:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1.C(OCC)(=O)C>C(#N)C>[O:38]1[CH2:39][CH2:40][N:35]([CH2:12][CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([C:20]3[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=3)[CH2:18][CH2:19]2)[CH2:36][CH2:37]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 86660669HCID 86660669, compound

Product 1

HCID 66584430HCID 66584430, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

The 4-tosyloxyethyl-N-(4-nitrophenyl)piperidine (2.02 g, 5.0 mmol) obtained in Example 6(2) was dissolved in acetonitrile (20 ml), and potassium carbonate (1.38 g, 10 mmol) and morpholine (0.65 ml, 7.5 mmol) were added thereto, followed by stirring at 80° C. for 15 hours. After the reaction mixture was allowed to cool to room temperature, ethyl acetate was added to the reaction mixture, and the organic layer was washed with water and saturated sodium chloride, and dried over anhydrous sodium sulfate. After the desiccant was filtered off, the residue obtained by evaporation under reduced pressure was purified using medium pressure silica gel flash column chromatography (methanol:chloroform=1:50 to 1:20), thereby obtaining 4-morpholinoethyl-N-(4-nitrophenyl)piperidine (1.23 g, 77%) as a yellow solid.

Workup

  1. temperatureto cool to room temperature
  2. washthe organic layer was washed with water and saturated sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter the desiccant was filtered off
  5. customthe residue obtained by evaporation under reduced pressure
  6. customwas purified

Sources & evidence

ORD record
ord-b378e0523fb94fee87080c84122f6df4
Source dataset
uspto-grants-2014_10
Patent number
US08865714B2

Reaction notes

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