Potassium Carbonate → Tert-butyl {6-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl}carbamate

HRID 1504768Notes

Reaction equation

HRID 1504768 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[N:8]=1)(=O)=O.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([CH2:6][C:7]2[N:8]=[C:9]([NH:13][C:14](=[O:15])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:10]=[CH:11][CH:12]=2)[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 19349110(6-(Tert-butoxycarbonylamino)pyridin-2-yl)methyl methanesulfonate

Product 1

HCID 86731662Tert-butyl {6-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl}carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution {6-[(tert-butoxycarbonyl)amino]pyridin-2-yl}methyl methanesulfonate (156 mg, 0.518 mmol) in acetonitrile (2.5 mL) was added N-methyl piperazine (103 mg, 1.03 mmol) and potassium carbonate (214 mg, 1.55 mmol) at room temperature. After 16 hours, the reaction mixture was quenched with saturated aqueous sodium bicarbonate, partially concentrated under reduced pressure, and then diluted with ethyl acetate. The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford tert-butyl {6-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl}carbamate that was used without further purification. MS ESI calc'd for C16H27N4O2 [M+H]+ 307. found 307.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous sodium bicarbonate
  2. concentrationpartially concentrated under reduced pressure
  3. additiondiluted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4bd29ced17fe435392db5cad3b2dc9fe
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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