Potassium Carbonate → Tert-butyl 4-(2-methoxy-2-oxoethyl)piperazine-1-carboxylate

HRID 2378626Notes

Reaction equation

HRID 2378626 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].Br[CH2:21][C:22]([O:24][CH3:25])=[O:23]>C(#N)C>[CH3:25][O:24][C:22](=[O:23])[CH2:21][N:17]1[CH2:16][CH2:15][N:14]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 46785870Tert-butyl 4-(2-methoxy-2-oxoethyl)piperazine-1-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (3.4 g, 25 mmol) was added to a mixture of N-Boc-piperazine (3.0 g, 16 mmol) in acetonitrile (20 mL). Methyl bromoacetate (1.5 mL, 16 mmol) was added to the mixture. Reaction stirred at room temperature for 1.5 hours. Mixture was filtered over celite. Filtrate was concentrated in vacuo. Residue was treated with diethyl ether (10 mL), filtered and concentrated in vacuo. Bulb to bulb distillation (165° C. at 700 mtorr) gave the title compound as clear colorless oil in 60% yield. MS m/e (M+H)+=259.4.

Workup

  1. customReaction
  2. filtrationMixture was filtered over celite
  3. concentrationFiltrate was concentrated in vacuo
  4. additionResidue was treated with diethyl ether (10 mL)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. distillationBulb to bulb distillation (165° C. at 700 mtorr)

Sources & evidence

ORD record
ord-3c40dbab2d3c4e8bb3b43508e557dd01
Source dataset
uspto-grants-2008_12
Patent number
US07470679B2

Reaction notes

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