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1-Piperazinecarboxylic acid, ethyl ester → Ethyl 4-(3-hydroxypropyl)piperazine-1-carboxylate

HRID 80737
Notes
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Reaction equation

HRID 80737 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].Br[CH2:13][CH2:14][CH2:15][OH:16].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([CH2:13][CH2:14][CH2:15][OH:16])[CH2:10][CH2:11]1)=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanol

Product 1

HCID 232657Ethyl 4-(3-hydroxypropyl)piperazine-1-carboxylateYield 76.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-piperazine carboxylic acid ethyl ester (25.50 g, 161.39 mmol), 3-bromo-1-propanol (22.43 g, 161.39 mmol), potassium carbonate (55.68 g, 403.48) and anhydrous acetonitrile (200 mL) were placed in a 500 mL round bottom flask, heated for refluxing and stirred overnight. The reaction was cooled down to room temperature, filtered, concentrated and subjected to a column chromatography (eluting agent: dichloromethane/methanol/triethylamine system, v/v/v 100:1:0.5) to obtain a light yellow oily substance, 26.60 g, yield 76.3%, which was directly used in the next step of reaction.

Workup

  1. temperatureheated
  2. temperaturefor refluxing
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washsubjected to a column chromatography (eluting agent: dichloromethane/methanol/triethylamine system, v/v/v 100:1:0.5)
  6. customto obtain a light yellow oily substance, 26.60 g, yield 76.3%, which
  7. customwas directly used in the next step of reaction

Sources & evidence

ORD record
ord-85a6c53532d546d8b8522b505ecd9aa1
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846678B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes