Piperidine → 2-(2-Nitro-5-piperdinylphenyl)-1,3-dioxolane

HRID 256179

Reaction equation

HRID 256179 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:7]=1.[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>>[N+:13]([C:5]1[CH:4]=[CH:3][C:2]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:7][C:6]=1[CH:8]1[O:12][CH2:11][CH2:10][O:9]1)([O-:15])=[O:14]

Participants

3

Reactant 2

HCID 8082PiperidineHCID 2673852-(5-Chloro-2-nitrophenyl)-1,3-dioxolane

Product 1

HCID 139875982-(2-Nitro-5-piperdinylphenyl)-1,3-dioxolaneYield 100%

Procedure

A mixture of 2-(5-chloro-2-nitrophenyl)-1,3-dioxolane (21.3 g, 0.09 mole) and piperidine (39.6 g, 0.46 mole) was heated at reflux in an oil bath. After 3 hours, excess piperidine was evaporated and the residue partitioned between water and dichloromethane. The organic phase was separated and the aqueous layer extracted with dichloromethane. Combined extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo to afford 2-(2-nitro-5-piperdinylphenyl)-1,3-dioxolane (21.6 g, 100%) as a dark colored oil which was used without further purification. An analytical sample was purified by flash chromatography using dichloromethane as eluant to give a light yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux in an oil bath
  3. customexcess piperidine was evaporated
  4. customthe residue partitioned between water and dichloromethane
  5. customThe organic phase was separated
  6. extractionthe aqueous layer extracted with dichloromethane
  7. washCombined extracts were washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-780747b03da34d5da4302f7cf0abbebe
Source dataset
uspto-grants-1987_10
Patent number
US04701459

Linked notes

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