Tert-Butylamine → 1-tert-Butyl-4-piperidone

HRID 1951448Notes

Reaction equation

HRID 1951448 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[I-].C([N+]1(C)[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1)C.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.O>[C:1]([N:5]1[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6385Tert-ButylamineHCID 516892Sodium BicarbonateHCID 110975681-Ethyl-1-methyl-4-oxopiperidin-1-ium iodide

Product 1

HCID 738401-tert-Butyl-4-piperidoneYield 60.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
78 °C

Procedure

To a solution of t-butylamine (78.2 ml, 0.74 mol) in toluene (400 ml) was added a solution of 1-ethyl-1-methyl-4-oxopiperidinium iodide (40 g, 0.148 mol) and sodium bicarbonate (1.245 g, 0.014 mol) in water (60 ml). The reaction mixture was heated at 78° C. for 6 hours and then allowed to cool to ambient temperature. The layers were separated and the aqueous layer was washed with EtOAc. The organics were combined and washed with brine, dried (MgSO4), filtered and reduced in vacuo to yield 1-tert-butyl-4-oxopiperidine (14 g) (LC/MS: Rt 0.39, [M+H]+ 156).

Workup

  1. temperatureto cool to ambient temperature
  2. customThe layers were separated
  3. washthe aqueous layer was washed with EtOAc
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-5e975682f90d47d790fa7f735e474193
Source dataset
uspto-grants-2013_03
Patent number
US08404718B2

Reaction notes

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