Triethylamine → 2-(Trimethylsilyl)ethyl 4-oxopiperidine-1-carboxylate

HRID 1864777Notes

Reaction equation

HRID 1864777 reaction equation
[CH3:1][Si:2]([CH3:19])([CH3:18])[CH2:3][CH2:4][O:5][C:6](=[O:17])OC1C=CC([N+]([O-])=O)=CC=1.C(N(CC)CC)C.Cl.[NH:28]1[CH2:33][CH2:32][C:31](=[O:34])[CH2:30][CH2:29]1>CN(C1C=CN=CC=1)C.C(#N)C>[CH3:19][Si:2]([CH3:1])([CH3:18])[CH2:3][CH2:4][O:5][C:6]([N:28]1[CH2:33][CH2:32][C:31](=[O:34])[CH2:30][CH2:29]1)=[O:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 30848514-Piperidone hydrochlorideHCID 30861164-Nitrophenyl 2-(trimethylsilyl)ethyl carbonate

Product 1

HCID 222659502-(Trimethylsilyl)ethyl 4-oxopiperidine-1-carboxylateYield 88.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

Carbonic acid 4-nitro-phenyl ester-2-trimethylsilanyl-ethyl ester (8.33 g, 29.3 mmol), triethylamine (12.3 g, 122 mmol) and DMAP (3.6 g, 29.5 mmol) were added to a room temperature solution of 4-piperidone hydrochloride (4.52 g, 33.4 mmol) in 100 mL of acetonitrile. The resulting mixture was heated at reflux for 2 h, then cooled and the volatiles were removed in vacuo. The residue was dissolved in dichloromethane, washed with water and 1M NaOH solution, and concentrated in vacuo to leave 6.3 g of product.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 2 h
  3. temperaturecooled
  4. customthe volatiles were removed in vacuo
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washwashed with water and 1M NaOH solution
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c6a7a3cd52434d208358e691aba60bf8
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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