Potassium Carbonate → 342435-23-8

HRID 1795155Notes

Reaction equation

HRID 1795155 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][O:14][CH3:15])[CH2:8][CH2:7]1)=O)C.N1CCC(C(OCC)=O)CC1.C(=O)([O-])[O-].[K+].[K+].COCCBr>C(O)C>[CH3:15][O:14][CH2:13][CH2:12][N:9]1[CH2:10][CH2:11][CH:6]([CH:4]=[O:3])[CH2:7][CH2:8]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 70770Ethyl 4-piperidinecarboxylateHCID 809722-Bromoethyl methyl etherHCID 21202762HCID 21202762, compound

Product 1

HCID 17893954342435-23-8Yield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(2-Methoxyethyl)-piperidine-4-carboxylic acid ethyl ester 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). The reaction mixture was heated to reflex for 24 hours, cooled and then filtered. The filtrate was concentrated in vacuo to yield the title compound (32.76 g, 92%); MS(ES+) m/e 216 [M+H]+. Step 2. 1-(2-Methoxyethyl)-piperidine-4-carbaldehyde Diisobutylaluminium hydride (10.2 ml, 1M solution in THF) was added to a solution of the product of Step 1 (2.0 g, 9.3 mmol) in toluene (40 ml) over a period of 1 hour at −78° C. The reaction was stirred at −78° C. for 1 hour and then quenched with methanol (5 ml) and aqueous ammonium acetate solution (5 ml). The mixture was stirred for 1 hour and then filtered through celite. The filtrate was concentrated in vacuo to yield the title compound (1.1 g, 69%); MS(ES+) m/e 172 [M+H]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-68b2c657a3274e07bac91e86fd8b822a
Source dataset
uspto-grants-2006_04
Patent number
US07026336B1

Reaction notes

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