Piperidine → 4-Methyl-1-(piperidin-1-YL)pentan-1-one

HRID 1912039Notes

Reaction equation

HRID 1912039 reaction equation
[CH3:1][CH:2]([CH3:8])[CH2:3][CH2:4][C:5]([OH:7])=O.[NH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>O.CN(C=O)C>[CH3:8][CH:2]([CH3:1])[CH2:3][CH2:4][C:5]([N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7]

Participants

7

Reactant 4

HCID 8082PiperidineHCID 12587Isocaproic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 229808734-Methyl-1-(piperidin-1-YL)pentan-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

4-Methylvaleric acid (238 g) and DMF (833 mL) were mixed. After an addition of piperidine (233 mL), HOBt.H2O (361 g) and WSC.HCl (452 g) to the mixture at ice temperature, the resulting mixture was stirred at RT overnight. To the reaction was added water (1000 mL) at ice temperature and the resulting mixture was extracted with toluene (500 mL×2). The organic layer was washed with aqueous 10 w/v % sodium carbonate (500 mL+300 mL) and water (500 mL×2). The organic layer was concentrated in vacuo to give the title compound (414.29 g) as a crude product.

Workup

  1. extractionthe resulting mixture was extracted with toluene (500 mL×2)
  2. washThe organic layer was washed with aqueous 10 w/v % sodium carbonate (500 mL+300 mL) and water (500 mL×2)
  3. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-e6ac6957f0574262993407896860be3e
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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