N,N'-Dimethylethylenediamine → 1-[4-(Aminomethyl)phenyl]piperidin-2-one

HRID 1009468Notes

Reaction equation

HRID 1009468 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC.I[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][NH2:23])=[CH:18][CH:17]=1.[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C:25]1=[O:30]>[Cu](I)I.C1(C)C=CC=CC=1>[NH2:23][CH2:22][C:19]1[CH:20]=[CH:21][C:16]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C:25]2=[O:30])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 126652-PiperidoneHCID 62657Potassium Phosphate, TribasicHCID 27375334-Iodobenzylamine

Product 1

HCID 47120251-[4-(Aminomethyl)phenyl]piperidin-2-oneYield 63%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 41 mg of copper iodide, 1.82 g of tripotassium phosphate, 38 mg of N,N′-dimethylethylenediamine, 1.00 g of 1-(4-iodophenyl)methyl amine, and 510 mg of 2-piperidone was added 4.29 mL of toluene, followed by stirring at 80° C. overnight under an argon atmosphere. The reaction liquid was filtered through Celite, the filtrate was then concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain 552 mg of 1-[4-(aminomethyl)phenyl]piperidine-2-one.

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered through Celite
  3. concentrationthe filtrate was then concentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-7629a09261744cf381eb482db56278fe
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

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