Water → 1-[2-(4-Nitrophenyl)ethyl]piperidine

HRID 1387776

Reaction equation

HRID 1387776 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[N+:10]([C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:5][CH:6]=1)([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 792664-Nitrophenethyl bromide

Product 1

HCID 2205731-[2-(4-Nitrophenyl)ethyl]piperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

In DMF (100 ml) was dissolved 4-(2-bromoethyl)nitro-benzene (25.0 g), and to the solution were added piperidine (12.9 ml) and potassium carbonate (18.0 g). The mixture was stirred at 70° C. for 15 hours, and to the mixture was added water (900 ml), and then the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate) to give 1-[2-(4-nitro-phenyl)ethyl]piperidine (24.8 g) as orange oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified with column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-08fe3290b2de451e933668c7389e859d
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Linked notes

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