Piperidine → 4,4-Dimethyl-1-piperidin-1-ylpentan-1-one

HRID 1912062Notes

Reaction equation

HRID 1912062 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[CH2:3][CH2:4][C:5]([OH:7])=O.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>O.CN(C=O)C>[CH3:8][C:2]([CH3:1])([CH3:9])[CH2:3][CH2:4][C:5]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:7]

Participants

7

Reactant 4

HCID 8082PiperidineHCID 142374,4-Dimethylpentanoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 539883484,4-Dimethyl-1-piperidin-1-ylpentan-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

4,4-Dimethylvaleric acid (348 g), piperidine (291 mL) and DMF (1.7 L) were mixed. To the mixture were added HOBt.H2O (450 g) and WSC.HCl (563 g) at ice temperature. After the mixture was stirred at RT overnight, water (1.7 L) was added to the reaction mixture at ice temperature and the mixture was extracted with toluene (500 mL, and 400 mL×2). The organic layer was washed with aqueous 10 w/v % sodium carbonate (1 L) and water (1 L), then concentrated in vacuo to give the title compound (508 g) as a crude product.

Workup

  1. extractionthe mixture was extracted with toluene (500 mL, and 400 mL×2)
  2. washThe organic layer was washed with aqueous 10 w/v % sodium carbonate (1 L) and water (1 L)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c2854455e34049cd909f59a0489cfc63
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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