Cesium carbonate → HCID 60980893, compound

HRID 1523722Notes

Reaction equation

HRID 1523722 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-].[Cs+].[Cs+].Br[CH2:19][CH2:20][CH2:21][O:22][CH3:23]>C(#N)C>[CH3:23][O:22][CH2:21][CH2:20][CH2:19][N:1]1[CH2:2][CH2:3][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 70770Ethyl 4-piperidinecarboxylateHCID 5245511-Bromo-3-methoxypropane

Product 1

HCID 60980893HCID 60980893, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of ethyl isonipecotate (22.0 grams, 140 mmol) in acetonitrile (250 mL) at room temperature was added cesium carbonate (97 grams, 298 mmol) followed by 1-bromo-3-methoxypropane (20 mL, 154 mmol) and the reaction mixture was heated to reflux for 4 hours. The reaction mixture was cooled to room temperature and filtered through a small pad of celite. The volatiles were removed under reduced pressure to obtain ethyl 1-(3-methoxy propyl)piperidin-4-carboxylate (31.0 grams).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. filtrationfiltered through a small pad of celite
  4. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-9185a581f34f4525aa99af6f127e4cb1
Source dataset
uspto-grants-2015_07
Patent number
US09079894B2

Reaction notes

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