Acetic Acid → 1-Boc-4-[2-(4-pyridinyl)ethyl]piperazine

HRID 23960

Reaction equation

HRID 23960 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:14]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)=[CH2:15].C(O)(=O)C>C(O)C>[C:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:15][CH2:14][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 75024-VinylpyridineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 223216311-Boc-4-[2-(4-pyridinyl)ethyl]piperazineYield 46.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Boc-piperazine (4.0 g, 21.5 mmol), 4-vinylpyridine (2.94 g, 27.9 mmol), and acetic acid (1.29 g, 21.5 mmol) were mixed in ethanol and heated to reflux for 48 h. The mixture was cooled to room temperature and concentrated under vacuum to provide 1-Boc-4-[2-(4-pyridinyl)ethyl]-piperazine (2.9 g, 45%) as an off white solid. The product was used without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux for 48 h
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0cbde3c2a82a4113837f2babf03f86ec
Source dataset
uspto-grants-2005_02
Patent number
US06855715B1

Linked notes

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