Potassium Carbonate → 1-(5-Bromopyridin-3-yl)-4-methylpiperazine

HRID 1507086

Reaction equation

HRID 1507086 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[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+]>CN(C=O)C>[Br:8][C:6]1[CH:7]=[C:2]([N:13]2[CH2:14][CH2:15][N:10]([CH3:9])[CH2:11][CH2:12]2)[CH:3]=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-Methylpiperazine2×HCID 693693,5-Dibromopyridine

Product 1

HCID 534853141-(5-Bromopyridin-3-yl)-4-methylpiperazineYield 79.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3,5-dibromopyridine (XXXVIII) (2.90 g, 12.24 mmol) in dry DMF (20 mL) was added 1-methylpiperazine (2.987 mL, 26.93 mmol) and K2CO3 (5.58 g, 40.39 mmol). The reaction was heated at 120° C. overnight. An additional portion of 1-methylpiperazine (6 mL) was added and heating was continued for another 24 h. The reaction was poured into ice water and filtered. The filtrate was extracted with 66% MeOH/CHCl3. The organic layer was dried over MgSO4, filtered and concentrated under vacuum to yield 1-(5-bromopyridin-3-yl)-4-methylpiperazine (XL) as a brown viscous oil (2.49 g, 9.76 mmol, 79.8% yield). ESIMS found for C10H14BrN3 m/z 256 (M+H).

Workup

  1. temperatureheating
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with 66% MeOH/CHCl3
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-12f271cef4614613ba7c200e1b74e37f
Source dataset
uspto-grants-2015_12
Patent number
US09221793B2

Linked notes

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