Triethylamine → Tert-butyl 2-(4-methylpiperazin-1-yl)acetate

HRID 2190264Notes

Reaction equation

HRID 2190264 reaction equation
Cl.Cl.[CH3:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.C(N(CC)CC)C.Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>C1COCC1.CCOC(C)=O.O>[CH3:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:6][CH2:5]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 79177tert-Butyl bromoacetateHCID 27347151-Methylpiperazine dihydrochloride

Product 1

HCID 11816730Tert-butyl 2-(4-methylpiperazin-1-yl)acetateYield 69%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1-methylpiperazine dihydrochloride (8.5 g, 49.2 mmol) and triethylamine (22.8 mL, 164.0 mmol) in THF (150 mL) was added tert-butyl 2-bromoacetate (8.0 g, 41.0 mmol). The mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted with EtOAc (200 mL) and H2O (100 mL). The organic phase was washed with brine, dried (MgSO4), filtered and concentrated to dryness. The residue was purified by column chromatography (silica, 0-10% MeOH in CH2Cl2) to afford the sub-title compound (6.0 g, 69%).

Workup

  1. washThe organic phase was washed with brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by column chromatography (silica, 0-10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-b14f599b32944708896dd32b07f1f230
Source dataset
uspto-grants-2012_12
Patent number
US08324264B1

Reaction notes

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