1-Methylpiperazine → HCID 71281048, compound

HRID 1045452Notes

Reaction equation

HRID 1045452 reaction equation
O=[CH:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([C:13]([O:15][CH2:16]C)=[O:14])=[CH:11][N:12]=2)[CH:9]=1.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([CH2:2][CH2:3][C:4]2[CH:5]=[CH:6][C:7]3[N:8]([C:10]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:12]=3)[CH:9]=2)[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 86677457HCID 86677457, compound

Product 1

HCID 71281048HCID 71281048, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of crude ethyl 6-(2-oxoethyl)imidazo[1,2-a]pyridine-3-carboxylate (112) (214 mg, 0.92 mmol) in DCM (5 mL) and 1-methylpiperazine (231 μL, 2.30 mmol) at room temperature was added portion-wise sodium triacetoxyborohydride (586 mg, 2.77 mmol). The reaction was stirred at room temperature overnight. The solvent was concentrated. The crude was taken in 10% sodium bicarbonate and ethyl acetate. The organic was washed with water, brine and dried over anhydrous sodium sulfate. The solvent was concentrated and the crude product was purified by silica chromatography to afford methyl 6-(2-(4-methylpiperazin-1-yl)ethyl)imidazo[1,2-a]pyridine-3-carboxylate (113). MS m/z 304.4 (M+1)+.

Workup

  1. concentrationThe solvent was concentrated
  2. washThe organic was washed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe solvent was concentrated
  5. customthe crude product was purified by silica chromatography

Sources & evidence

ORD record
ord-c8a6e5f1dc8f4387aac77ca3b582c2a9
Source dataset
uspto-grants-2013_10
Patent number
US08569283B2

Reaction notes

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