tert-Butyl piperazine-1-carboxylate → t-Butyl 4-(6-chloromethylpyridin-2-ylmethyl)piperazine-1-carboxylate

HRID 1668518

Reaction equation

HRID 1668518 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][Cl:10])[N:4]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>C(O)C>[Cl:10][CH2:9][C:5]1[N:4]=[C:3]([CH2:2][N:21]2[CH2:20][CH2:19][N:18]([C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:17])[CH2:23][CH2:22]2)[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 3166542,6-Bis(chloromethyl)pyridine

Product 1

HCID 58105228t-Butyl 4-(6-chloromethylpyridin-2-ylmethyl)piperazine-1-carboxylateYield 38.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,6-Bis(chloromethyl)pyridine (352 mg) was suspended in 4 mL of ethanol, and 372 mg of N-(t-butoxycarbonyl)piperazine was added into the suspension at ice temperature, and then the suspension was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, the residue was added to water and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was removed. The residue was purified by chromatography on silica gel (methylene chloride-ethanol=30:1) to give 250 mg of t-butyl 4-(6-chloromethylpyridin-2-ylmethyl)piperazine-1-carboxylate as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was added to water
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed
  7. customThe residue was purified by chromatography on silica gel (methylene chloride-ethanol=30:1)

Sources & evidence

ORD record
ord-da6258bb609641c28feb59f6b6ced1c4
Source dataset
uspto-grants-2011_08
Patent number
US07989446B2

Linked notes

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