Butylamine → 1-Butyl-4-piperidone

HRID 1586449Notes

Reaction equation

HRID 1586449 reaction equation
O.Cl.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.[CH2:10](N)[CH2:11][CH2:12][CH3:13].C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.O.CO>[CH2:10]([N:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)[CH2:11][CH2:12][CH3:13]

Participants

8

Reactant 4

HCID 8007ButylamineHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 2723901Piperonylamine

Product 1

HCID 899951-Butyl-4-piperidoneYield 62.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-piperidone hydrochloride monohydrate (20.6 g) and n-butylamine (25.0 g) in methylene chloride (300 ml) was added triethylamine (63 ml), and the mixture was stirred at room temperature for 12 hours. Methanol was further added to the reaction solution, and the solution was made uniform. To the solution were added water (7 ml) and anhydrous potassium carbonate (21.1 g), and the mixture was stirred for 30 minutes. The reaction solution was filtered off with Celite, and then the solvent was distilled off under reduced pressure. The residue obtained was purified by silica gel column chromatography (chloroform:methanol=10:1) to give the title compound (13.0 g) as a yellow oily substance. Yield=62%.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. filtrationThe reaction solution was filtered off with Celite
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue obtained
  5. customwas purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-9229248a19b740e3b5767c1ab97ade57
Source dataset
uspto-grants-1999_08
Patent number
US05945434

Reaction notes

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