Water → HCID 66711551, compound

HRID 1261943Notes

Reaction equation

HRID 1261943 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH:17]1[CH2:22][CH2:21][CH:20]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH2:19][CH2:18]1.O>CS(C)=O.C(OCC)(=O)C>[N+:8]([C:4]1[CH:3]=[C:2]([N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH2:19][CH2:18]2)[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 98231-Fluoro-3-nitrobenzeneHCID 11430Potassium CarbonateHCID 7957244-Morpholinopiperidine

Product 1

HCID 66711551HCID 66711551, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

1-Fluoro-3-nitro-benzene (1.00 g, 0.00709 mol) and Potassium carbonate (1.47 g, 0.0106 mol) were dissolved in Dimethyl sulfoxide (7.50 mL) and 4-Piperidin-4-yl-morpholine (2.41 g, 0.0142 mol) was added. The reaction was allowed to stir overnight at 90° C. Upon completion of the reaction, the mixture was diluted with ethyl acetate and was poured over water. Combined extracts were then washed with brine and the organics were dried over magnesium sulfate, filtered and reduced. The crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate). Combined fractions were reduced en vacuo to afford 1.60 g of 4-[1-(3-Nitro-phenyl)-piperidin-4-yl]-morpholine.

Workup

  1. customUpon completion of the reaction
  2. washCombined extracts were then washed with brine
  3. dry with materialthe organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate)

Sources & evidence

ORD record
ord-2680da4caceb49a0b845daa12f7422dc
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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