Cyclopropylamine → 1-Cyclopropylpiperidin-4-one

HRID 2234356Notes

Reaction equation

HRID 2234356 reaction equation
[I-].[CH2:2]([N+:4]1(C)[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1)[CH3:3].[CH:12]1(N)CC1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.O>[CH:2]1([N:4]2[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]2)[CH2:3][CH2:12]1

Participants

6

Reactant 3

HCID 69828CyclopropylamineHCID 516892Sodium BicarbonateHCID 110975681-Ethyl-1-methyl-4-oxopiperidin-1-ium iodide

Product 1

HCID 162276291-Cyclopropylpiperidin-4-oneYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
78 °C

Procedure

1-Ethyl-1-methyl-4-oxopiperidinium iodide (Journal of the Chemical Society (1949), 708-15; 15 g, 55.74 mmol) was added to cyclopropylamine (Aldrich; 19.3 mL, 278.69 mmol) in toluene (150 mL). Sodium hydrogen carbonate (469 mg, 5.57 mmol) in water (21 mL) was added and the mixture heated at 78° C. over night. The mixture was cooled and the layers separated. The aqueous layer was extracted (×2) with ethyl acetate and the combined organics washed with brine, dried (MgSO4) and concentrated. Column chromatography of the residue (2% MeOH/DCM) gave the title compound (4.1 g, 53%) as a pale brown liquid.

Workup

  1. temperatureThe mixture was cooled
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted (×2) with ethyl acetate
  4. washthe combined organics washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4e775eb0c09d4dfd8dd2d4b184e2f1ee
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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