Acetone → Ethyl 1-isopropylpiperidine-4-carboxylate

HRID 1882940Notes

Reaction equation

HRID 1882940 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.[CH3:12][C:13]([CH3:15])=O>[Pd].C(O)C>[CH:13]([N:1]1[CH2:2][CH2:3][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:10][CH2:11]1)([CH3:15])[CH3:12]

Participants

5

Reactant 2

HCID 180AcetoneHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 19900430Ethyl 1-isopropylpiperidine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
35 °C

Procedure

An autoclave was charged with ethyl isonipecotate (50 g, 318.0 mmol), 10% Pd/C (5 g, 10 wt %), acetone (450 mL, 6.13 mol) and ethanol (100 mL). The autoclave was pressurized to 4.1 bar with H2, and the slurry was heated to 35° C. After 14 h the mixture was filtered, rinsed with acetone, and was concentrated to remove excess acetone. The crude material was taken on without any purification:

Workup

  1. filtrationAfter 14 h the mixture was filtered
  2. washrinsed with acetone
  3. concentrationwas concentrated
  4. customto remove excess acetone
  5. customThe crude material was taken on without any purification

Sources & evidence

ORD record
ord-861d9b482893434cb157052cfcd029c3
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

Loading…