tert-Butyl 4-(2-chloroethyl)piperazinecarboxylate → tert-Butyl 4-(2-(methylamino)ethyl)piperazine-1-carboxylate

HRID 856083Notes

Reaction equation

HRID 856083 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.CO.[CH3:19][NH2:20]>CO>[CH3:19][NH:20][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 22106269tert-Butyl 4-(2-chloroethyl)piperazinecarboxylateHCID 57454252Monomethylamine methanol

Product 1

HCID 23081391tert-Butyl 4-(2-(methylamino)ethyl)piperazine-1-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Tert-butyl 4-(2-chloroethyl)piperazine-1-carboxylate (3.13 g, 12.58 mmol) was dissolved in methanol (20 ml), to which 40% methylamine methanol solution (30 ml) was added, and the mixture was heated under reflux for 5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methylene chloride. The mixture was washed with saturated sodium hydrogencarbonate aqueous solution. The organic layer was dried over magnesium sulfate, and then filtered, and the filtrate was concentrated under reduced pressure to afford tert-butyl 4-(2-methylaminoethyl)piperazine-1-carboxylate (3.0 g, yield 98%) as a pale yellow oil.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 5 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in methylene chloride
  6. washThe mixture was washed with saturated sodium hydrogencarbonate aqueous solution
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-706d8394160b4315bd33841d9aca6d42
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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