2-Chloropyridine → (3R)-3-methyl-1-pyridin-2-ylpiperazine

HRID 888170Notes

Reaction equation

HRID 888170 reaction equation
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.Cl[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1>C1(C)C(C)=CC=CC=1>[CH3:1][C@H:2]1[NH:3][CH2:4][CH2:5][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH2:7]1

Participants

4

Reactant 2

HCID 79772-ChloropyridineHCID 73304342-Methylpiperazine, (R)-

Product 1

HCID 1519493(3R)-3-methyl-1-pyridin-2-ylpiperazineYield 40.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a solution of (R)-2-methyl piperazine (6.6 g, 0.066 mol) in xylene (100 mL) at 140° C. under nitrogen was added 2-chloro pyridine (4 g, 0.035 mol) slowly over a period of 1 h. The heating was continued for additional 12 h and cooled to RT. The solvent was removed under reduced pressure and the resulting residue was purified by chromatography using chloroform methanol (8/2) as eluent to afford the title product as a liquid (2.5 g, 40%). TLC-Chloroform/MeOH (8/2); Rf=0.2. HPLC purity: 97%.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe resulting residue was purified by chromatography

Sources & evidence

ORD record
ord-a0d01c24c15643f880827f242cf68691
Source dataset
uspto-grants-2012_08
Patent number
US08247437B2

Reaction notes

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