1-Piperazinecarboxylic acid, ethyl ester → HCID 86712833, compound

HRID 1486790Notes

Reaction equation

HRID 1486790 reaction equation
[N:1]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 11430Potassium CarbonateHCID 1187091-Pentanol, 5-bromo-

Product 1

HCID 86712833HCID 86712833, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl N-piperazinecarboxylate (25.50 g, 161.39 mmol), 5-bromo-1-pentanol (26.96 g, 161.39 mmol), potassium carbonate (55.68 g, 403.48 mmol) and anhydrous acetonitrile (200 mL) were placed in a 500 mL round-bottomed flask and heated under reflux with stirring overnight; the reaction system was cooled down to room temperature, filtered, concentrated and separated by column chromatography (eluent: dichloromethane/methanol/triethylamine system, v/v/v 100:1:0.5), to obtain a pale yellow oil 20.48 g, yield 52.0% (which was directly used in the next step reaction).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customseparated by column chromatography (eluent: dichloromethane/methanol/triethylamine system, v/v/v 100:1:0.5)

Sources & evidence

ORD record
ord-cb9342a1a0d4402cb5cb96e391e19395
Source dataset
uspto-grants-2016_08
Patent number
US09428496B2

Reaction notes

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