Acetic Acid → 1-Methyl-4-[2-(pyridin-4-yl)ethyl]piperazine

HRID 494015Notes

Reaction equation

HRID 494015 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)=[CH2:2].[CH3:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(O)(=O)C.[OH-].[Na+]>C(O)C>[CH3:9][N:10]1[CH2:15][CH2:14][N:13]([CH2:2][CH2:1][C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 75024-VinylpyridineHCID 14798Sodium HydroxideHCID 531671-Methylpiperazine

Product 1

HCID 207588501-Methyl-4-[2-(pyridin-4-yl)ethyl]piperazineYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
160 °C

Procedure

In a tube, 2 ml (19 mM) of 4-vinylpyridine, 3.16 ml (28.5 mM) of N-methylpiperazine, and 200 μl of acetic acid are mixed in 12 ml of ethanol. The tube is closed and heated for 10 minutes at 160° C. in a microwave oven. After cooling, 20 ml of 0.5N sodium hydroxide are added slowly and the mixture is extracted with dichloromethane. The separated organic phase is dried over magnesium sulphate and concentrated under reduced pressure. The product sought after is thus obtained as a yellow oil (yield=86%).

Workup

  1. customThe tube is closed
  2. temperatureAfter cooling
  3. extractionthe mixture is extracted with dichloromethane
  4. dry with materialThe separated organic phase is dried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-487a6d0cad9a41dcb06fa13f18cf8e80
Source dataset
uspto-grants-2009_05
Patent number
US07538111B2

Reaction notes

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