Trifluoroacetic acid → (3S)-3-methyl-1-pyridin-2-ylpiperazine

HRID 1403510Notes

Reaction equation

HRID 1403510 reaction equation
[CH3:1][C@H:2]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:5][CH2:4][N:3]1C(OC(C)(C)C)=O.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:1][C@@H:2]1[NH:3][CH2:4][CH2:5][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:7]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 70665341(S)-tert-butyl 2-methyl-4-(pyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 1519492(3S)-3-methyl-1-pyridin-2-ylpiperazineYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 2-methyl-4-(pyridin-2-yl)piperazine-1-carboxylate (5.2 g, 18.75 mmol,) in dichloromethane (30 ml) was added trifluoroacetic acid (5 ml). After stirring overnight at room temperature, the pH was adjusted to 8 with an aqueous sodium carbonate solution, extracted with dichloromethane (3×150 ml), dried over anhydrous magnesium sulfate and concentrated under vacuum to afford (S)-3-methyl-1-(pyridin-2-yl)piperazine as yellow oil (3.1 g, 93%).

Workup

  1. extractionextracted with dichloromethane (3×150 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2a0cf015eeef45a99717ea2a1313e154
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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