Potassium Carbonate → HCID 21202762, compound

HRID 2223098Notes

Reaction equation

HRID 2223098 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.C(=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][CH2:20][CH2:21]Br>C(O)C>[CH2:8]([O:7][C:5]([CH:4]1[CH2:3][CH2:2][N:1]([CH2:21][CH2:20][O:19][CH3:18])[CH2:11][CH2:10]1)=[O:6])[CH3:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70770Ethyl 4-piperidinecarboxylateHCID 809722-Bromoethyl methyl ether

Product 1

HCID 21202762HCID 21202762, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl isonipecotate (26 g, 166 mmol) in ethanol (150 ml) was treated with potassium carbonate (41 g, 297 mmol) and 2-bromoethyl methyl ether (25 g, 179 mmol). After heating at reflux for 24 hours, the mixture was filtered and the solid washed with ethanol. The filtrate was concentrated in vacuo to yield the title compound (32.76 g, 92%); 1H NMR (CDCl3) 4.12 (2H, q, J=7.1 Hz), 3.51 (2H, t, J=5.7 Hz), 3.33 (3H, s), 2.92 (2H, m), 2.56 (2H, t, J=5.7 Hz), 2.33-1.71 (7H, m) and 1.25 (3H, t, J7.1 Hz).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 24 hours
  3. filtrationthe mixture was filtered
  4. washthe solid washed with ethanol
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-faa11dca286a42819d4b0eff4f560e88
Source dataset
uspto-grants-2008_05
Patent number
US07375105B2

Reaction notes

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