Triethylamine → 2-(4-ethoxycarbonyl-1-piperidinyl)-4-nitropyridine N-oxide

HRID 347727Notes

Reaction equation

HRID 347727 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][N+:3]=1[O-:11].[CH2:12]([O:14][C:15]([CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16])[CH3:13].C(N(CC)CC)C>C(O)C>[CH2:12]([O:14][C:15]([CH:17]1[CH2:22][CH2:21][N:20]([C:2]2[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][N+:3]=2[O-:11])[CH2:19][CH2:18]1)=[O:16])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylateHCID 39040262-Bromo-4-nitropyridine N-oxide

Product 1

HCID 588011162-(4-ethoxycarbonyl-1-piperidinyl)-4-nitropyridine N-oxideYield 111.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-bromo-4-nitropyridine N-oxide (12 g), which is prepared according to the method disclosed in J. Org. Chem., 21, 1077 (1956), in ethanol (300 ml) are added 4-piperidinecarboxylic acid ethyl ester (22 g) and triethylamine (11.6 ml), and the mixture is stirred at 80° C. for 5 hours. The reaction solution is concentrated under reduced pressure, and the residue is dissolved in ethyl acetate, washed with water, and the solvent is evaporated under reduced pressure to give the title compound (18 g).

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washwashed with water
  4. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-b2122ce626dd47209bab860b2c95742e
Source dataset
uspto-grants-2007_02
Patent number
US07176199B2

Reaction notes

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