Acetic Anhydride → Methyl 1-acetyl-4-oxopiperidine-3-carboxylate

HRID 1930572Notes

Reaction equation

HRID 1930572 reaction equation
Cl.[O:2]=[C:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH:4]1[C:9]([O:11][CH3:12])=[O:10].C(N(CC)CC)C.[C:20](OC(=O)C)(=[O:22])[CH3:21]>ClCCl>[C:20]([N:6]1[CH2:7][CH2:8][C:3](=[O:2])[CH:4]([C:9]([O:11][CH3:12])=[O:10])[CH2:5]1)(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 2724028Methyl 4-oxopiperidine-3-carboxylate hydrochloride

Product 1

HCID 14143329Methyl 1-acetyl-4-oxopiperidine-3-carboxylateYield 59.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 4-oxo-3-piperidinecarboxylate hydrochloride (10 g, 51.65 mmol) was dissolved in dichloromethane (130 mL). Triethylamine (7.20 mL, 51.65 mmol) was added followed by acetic anhydride (4.87 mL, 51.65 mmol). The reaction mixture was stirred at room temperature for 2 h. The organic phase was washed with water, dried over MgSO4, filtered and concentrated to give methyl 1-acetyl-4-oxopiperidine-3-carboxylate (6.10 g, 59.3%), which was used in the next step as such.

Workup

  1. washThe organic phase was washed with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-978d97d6eed743db870ed37c272c7d22
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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