Sodium Iodide → HCID 14987937, compound

HRID 1494270Notes

Reaction equation

HRID 1494270 reaction equation
[N:1]1([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].[CH:23]1(Br)[CH2:27][CH2:26][CH2:25][CH2:24]1.[Na+].[I-]>CN(C=O)C.O>[CH:23]1([N:4]2[CH2:3][CH2:2][N:1]([C:7]3[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][N:8]=3)[CH2:6][CH2:5]2)[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8728BromocyclopentaneHCID 10340Sodium CarbonateHCID 14987928Methyl 6-piperazinonicotinate2×

Product 1

HCID 14987937HCID 14987937, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.21 g of methyl 6-piperazinylnicotinate (compound 6), 3.18 g of sodium carbonate and 1.64 g of cyclopentyl bromide 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 150 ml of water and extracted 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; ethyl acetate) afforded 1.73 g of methyl 6-(4 -cyclopentyl-1-piperazinyl)nicotinate (yield 60%).

Workup

  1. temperatureThe mixture was heated to 120°-130° C.
  2. extractionextracted 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; ethyl acetate)

Sources & evidence

ORD record
ord-71637a9124c14e889f7493b4d3c60180
Source dataset
uspto-grants-1991_06
Patent number
US05025012

Reaction notes

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