Pyridine → tert-Butyl 4-(methylcarbamoyl)piperazine-1-carboxylate

HRID 1257103Notes

Reaction equation

HRID 1257103 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14](Cl)=[O:15])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N:17]1C=CC=C[CH:18]=1.CN>ClCCl>[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:15])[NH:17][CH3:18])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6329MethylamineHCID 11334154Tert-butyl 4-(chlorocarbonyl)piperazine-1-carboxylate

Product 1

HCID 20768834tert-Butyl 4-(methylcarbamoyl)piperazine-1-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-Boc-4-(chlorocarbonyl)piperazine (300 mg, 1.22 mmol), pyridine (288.4 mg, 3 equiv), and methylamine (1.83 mmol, 1.5 equiv) in dichloromethane was refluxed overnight. The solution was quenched by the dropwise addition of water. The organic layer was separated, dried over anhydrous Na2SO4, and evaporated in vacuo. The residue was purified by flash chromatography to give the title compound as a solid (˜70% yield).

Workup

  1. customThe solution was quenched by the dropwise addition of water
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous Na2SO4
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-174f1e715bad44828618a05446b48794
Source dataset
uspto-grants-2013_06
Patent number
US08461339B2

Reaction notes

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