4-Methylidene-1-(4-nitrophenyl)piperidine → HCID 67106225, compound

HRID 1910825Notes

Reaction equation

HRID 1910825 reaction equation
[CH2:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1>C(OCC)(=O)C>[CH2:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 1

HCID 671069544-Methylidene-1-(4-nitrophenyl)piperidine

Product 1

HCID 67106225HCID 67106225, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-methylene-1-(4-nitrophenyl)-piperidine (230 mg, 1.05 mmol) in ethyl acetate (5 mL) was added stannous chloride dihydrate (1.19 g, 5.2 mmol). The mixture was heated to 60° C. and maintained for 4 hrs. The mixture was evaporated to dryness then sodium hydroxide solution was added to give a final pH of 8. The mixture was extracted with ethyl acetate and the combined organic layers were washed with water, then brine, and then dried. Concentration under reduced pressure afforded 4-methylene-1-(4-aminophenyl)-piperidine (150 mg, 75%) as a semisolid.

Workup

  1. temperaturemaintained for 4 hrs
  2. customThe mixture was evaporated to dryness
  3. additionsodium hydroxide solution was added
  4. customto give a final pH of 8
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe combined organic layers were washed with water
  7. dry with materialbrine, and then dried
  8. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-5cd2ad4c006f433eb11f6f2d0064f6a8
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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