Dimethylamine → tert-Butyl 4-(dimethylcarbamoyl)piperazine-1-carboxylate

HRID 1257105Notes

Reaction equation

HRID 1257105 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]1[CH:22]=CC=C[CH:18]=1.CNC>ClCCl>[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:15])[N:17]([CH3:22])[CH3:18])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 1049PyridineHCID 11334154Tert-butyl 4-(chlorocarbonyl)piperazine-1-carboxylate

Product 1

HCID 22665738tert-Butyl 4-(dimethylcarbamoyl)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) (Preparation B-12-A), and dimethylamine (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-e1427a989f3945f59ad695a1b181e64a
Source dataset
uspto-grants-2013_06
Patent number
US08461339B2

Reaction notes

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