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

HRID 901100

Reaction equation

HRID 901100 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 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of (bromomethyl)cyclopropane (500 mg, 4 mmol, 1.0 eq.) and 4-piperidone hydrate hydrochloride (579 mg, 4 mmol, 1.0 eq.) in acetonitrile (30 mL) was added sodium carbonate (1.148 g, 11 mmol, 3. eq.). 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 (62%) of the tide 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-a2ae8eef1ddf4083bab3acff954328f8
Source dataset
uspto-grants-2008_04
Patent number
US07361682B2

Linked notes

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