Sodium Iodide → Methyl 6-(4-methylpiperazin-1-yl)pyridine-3-carboxylate

HRID 1494269Notes

Reaction equation

HRID 1494269 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(NC(C)C)(C)C.[Na+].[I-]>CN(C=O)C.O>[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=2)[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7912DiisopropylamineHCID 531671-MethylpiperazineHCID 254249Methyl 6-chloropyridine-3-carboxylate

Product 1

HCID 9859497Methyl 6-(4-methylpiperazin-1-yl)pyridine-3-carboxylateYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5.15 g of methyl 6-chloronicotinate, 3.15 g of 1-methylpiperazine and 3.18 g of diisopropylamine in 50 ml of DMF was added a catalytic amount of NaI. The mixture was heated to 120°-130° C. and stirred for 4 hours. The resulting mixture was poured into 250 ml of water followed by extraction with ethyl acetate. The extract was washed twice with water, and once with a saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate and concentrated. Purification of the concentrate by column chromatography (silica gel; chloroform:methanol=3:1) afforded 5.39 g of methyl 6-(4-methyl-1-piperazinyl)nicotinate (yield 77%).

Workup

  1. temperatureThe mixture was heated to 120°-130° C.
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract was washed twice with water
  4. dry with materialonce with a saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customPurification of the
  7. concentrationconcentrate by column chromatography (silica gel; chloroform:methanol=3:1)

Sources & evidence

ORD record
ord-7d04b06c38844d36956240af68f83872
Source dataset
uspto-grants-1991_06
Patent number
US05025012

Reaction notes

Loading…