Hydrochloric Acid → 1,2-Diethyl-4-piperidinone

HRID 232274

Reaction equation

HRID 232274 reaction equation
C[Si](C)(C)[O:3][C:4]([CH:6]=[CH2:7])=[CH2:5].[CH2:10]([NH:12][CH2:13][CH2:14][CH3:15])[CH3:11].B(F)(F)F.CCOCC.Cl>C(Cl)Cl>[CH2:10]([N:12]1[CH2:7][CH2:6][C:4](=[O:5])[CH2:3][CH:13]1[CH2:14][CH3:15])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 883981-Propanamine, N-ethyl-HCID 5546572-(Trimethylsiloxy)-1,3-butadiene

Product 1

HCID 200313151,2-Diethyl-4-piperidinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 100 mL of methylene chloride cooled to 0° C. is added 2-(trimethylsilyloxy)-1,3-butadiene (14.2 g, 0.1 mol), 8.5 g (0.1 mol) of N-ethyl-propanamine, and 14.2 g (0.1 mol) of borontrifluoride etherate. Monitor the reaction by thinlayer chromatography. Upon completion add 1N HCl until gas evolution ceases. Separate the aqueous layer and make it alkaline with 1N NaOH. Extract twice with 100 mL ether and dry over Na2SO4. Filter the drying agent and evaporated the solvent in vacuo to obtain the title compound.

Workup

  1. customMonitor the reaction by thinlayer chromatography
  2. customSeparate the aqueous layer
  3. extractionExtract twice with 100 mL ether
  4. dry with materialdry over Na2SO4
  5. filtrationFilter the drying agent
  6. customevaporated the solvent in vacuo

Sources & evidence

ORD record
ord-dc7eb3e1a8054954978500e3c6bd556b
Source dataset
uspto-grants-1989_07
Patent number
US04851526

Linked notes

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