Hydrochloric Acid → 4-Ethyl-1-piperidin-1-ylhexan-1-one

HRID 1912086Notes

Reaction equation

HRID 1912086 reaction equation
[CH2:1]([CH:3]([CH2:9][CH3:10])[CH2:4][CH2:5][C:6]([OH:8])=O)[CH3:2].[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl>CN(C=O)C.C(OCC)(=O)C.O>[CH2:9]([CH:3]([CH2:1][CH3:2])[CH2:4][CH2:5][C:6]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:8])[CH3:10]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 227344-Ethylhexanoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 711147404-Ethyl-1-piperidin-1-ylhexan-1-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Ethylhexanoic acid (47.0 g) was dissolved in DMF (190 mL). To the solution were added piperidine (34.0 mL), HOBt.H2O (52.7 g) and WSC.HCl (66.1 g). The mixture was stirred at RT overnight. To the reaction mixture were added ethyl acetate (300 mL) and 1 N hydrochloric acid (100 mL) at ice temperature. The aqueous layer was removed and the organic layer was washed with saturated aqueous sodium bicarbonate (150 mL×2) and brine (100 mL×2), then dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate was concentrated in vacuo to give the title compound (59.8 g) as a crude product.

Workup

  1. customThe aqueous layer was removed
  2. washthe organic layer was washed with saturated aqueous sodium bicarbonate (150 mL×2) and brine (100 mL×2)
  3. dry with materialdried over sodium sulfate
  4. filtrationThe sodium sulfate was filtered off
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9c15ed0eab8f43feae738e6ee59f471a
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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