Potassium Carbonate → 5-Bromo-2-(4-methylpiperazin-1-yl)pyridine

HRID 1910677Notes

Reaction equation

HRID 1910677 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:13]2[CH2:14][CH2:15][N:10]([CH3:9])[CH2:11][CH2:12]2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 27344145-Bromo-2-chloropyridine

Product 1

HCID 164142065-Bromo-2-(4-methylpiperazin-1-yl)pyridineYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

5-Bromo-2-chloropyridine (1.0 g), N-methylpiperazine (1.56 g, 3 eq), and potassium carbonate (2.16 g, 3 eq) were combined in N-methylpyrrolidinone (5 mL) and heated to 120° C. overnight. The crude mixture was then cooled to room temperature and diluted with water. The solid product was collected by filtration, then washed with more water and dried under vacuum (824 mg, 62% yield). 1H-NMR (300 MHz, CDCl3) δ 8.18 (d, 1H), 7.50 (dd, 1H), 6.53 (d, 1H), 3.50 (m, 4H), 2.50 (m, 4H), 2.33 (s, 3H).

Workup

  1. filtrationThe solid product was collected by filtration
  2. washwashed with more water
  3. customdried under vacuum (824 mg, 62% yield)

Sources & evidence

ORD record
ord-0516350a869b49969d825c6b2fadf202
Source dataset
uspto-grants-2013_12
Patent number
US08604023B2

Reaction notes

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