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

HRID 272557
Notes
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Reaction equation

HRID 272557 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-6f8c09e36221499a9402e63f834e28db
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07456174B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes