Sodium Carbonate → 1-(Cyclopropylmethyl)piperidin-4-one

HRID 2354987Notes

Reaction equation

HRID 2354987 reaction equation
Br[CH2:2][CH:3]1[CH2:5][CH2:4]1.Cl.O.[NH:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH:5]1([CH2:4][N:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 81503BromomethylcyclopropaneHCID 2723901Piperonylamine

Product 1

HCID 180021811-(Cyclopropylmethyl)piperidin-4-oneYield 55.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of bromomethyl cyclopropane (4 mmol) and 4-piperidone hydrate hydrochloride (4 mmol) in acetonitrile (30 mL) was added sodium carbonate (11 mmol). The reaction mixture was stirred 16 h at 85° C. The resulting suspension was filtered and the solid was washed with acetonitrile. The filtrate was concentrated in vacuo and purified by column chromatography on silica eluting with DCM/2N NH3 in methanol 97:3 to yield 339 mg of the title compound as yellow oil. MS (m/e): 154.2 (MH+, 100%).

Workup

  1. filtrationThe resulting suspension was filtered
  2. washthe solid was washed with acetonitrile
  3. concentrationThe filtrate was concentrated in vacuo
  4. custompurified by column chromatography on silica eluting with DCM/2N NH3 in methanol 97:3

Sources & evidence

ORD record
ord-a4e137a9ee4d48ec941caf015a65470d
Source dataset
uspto-grants-2010_07
Patent number
US07754736B2

Reaction notes

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