Acetic Acid → 2-Methyl-4-piperidinone acetate

HRID 2179394

Reaction equation

HRID 2179394 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH:9]1[CH3:15])C1C=CC=CC=1.[C:16]([OH:19])(=[O:18])[CH3:17]>[Pd]>[C:16]([OH:19])(=[O:18])[CH3:17].[CH3:15][CH:9]1[CH2:10][C:11](=[O:14])[CH2:12][CH2:13][NH:8]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 110957071-Benzyl-2-methylpiperidin-4-one

Product 1

HCID 666845422-Methyl-4-piperidinone acetateYield 99%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of the product of step B (3.8 g, 18.7 mmol) in acetic acid (20 mL) was added Pd/C 10% (380 mg) cautiously. The resulting mixture was hydrogenated at 50 psi H2 for 3 h. The reaction mixture was filtered through celite and washed with acetic acid (20 mL). The filtrate was concentrated in vacuo to yield 2-methylpiperidin-4-one acetate as a brown oil (2.98 g, >99%) which was sufficiently pure for the next step: 1H NMR (CD3OD, 400 MHz) δ 3.24-3.19 (m, 1H), 2.86-2.81 (m, 1H), 2.74-2.67 (m, 1H), 2.51-2.49 (m, 2H), 2.37-2.28 (m, 2H), 2.22-2.18 (m, 1H), 2.12-2.02 (m, 2H), 1.08 (d, J=6.4 Hz, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with acetic acid (20 mL)
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e1c68e2827b44da0962e2bcf4acbee36
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Linked notes

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