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

HRID 1985485Notes

Reaction equation

HRID 1985485 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-0a0884dd9c864de29e7d918692d3ee45
Source dataset
uspto-grants-2009_06
Patent number
US07544680B2

Reaction notes

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