Potassium Carbonate → HCID 914998, compound

HRID 1629655Notes

Reaction equation

HRID 1629655 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:10][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:10][N:11]1[CH2:16][CH2:15][N:14]([CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 914998HCID 914998, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of ethyl 4-bromobutanoate (5.75 g, 29.5 mmol; Aldrich No.167118) and 1-methylpiperazine (3.55 mL, 32.0 mmol; Aldrich No. 130001) and anhydrous K2CO3 (4.5 g, 32.5 mmol; Fisher No. P208) in acetonitrile (MeCN, 150 mL) was refluxed for 18 h before concentrated in vacuo. The organic layer was then separated and the aqueous layer was extracted with dichloromethane (DCM, 3×150 mL). The combined organic extracts were washed with water (150 mL), dried (Na2SO4), and concentrated in vacuo to give ethyl 4-(4-methylpiperzin-1-yl)butanoate (6.01 g, 96%) as a yellow oil.

Workup

  1. temperaturewas refluxed for 18 h
  2. concentrationbefore concentrated in vacuo
  3. customThe organic layer was then separated
  4. extractionthe aqueous layer was extracted with dichloromethane (DCM, 3×150 mL)
  5. washThe combined organic extracts were washed with water (150 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f2ea559b445b47318dcbc3545a77849f
Source dataset
uspto-grants-2014_07
Patent number
US08790691B2

Reaction notes

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