Ethyl piperazine-1-acetate → Ethyl [4-(1,1-Dimethyl-2-oxo-ethyl)-piperazin-1-yl]-acetate

HRID 488415Notes

Reaction equation

HRID 488415 reaction equation
Br[C:2]([CH3:6])([CH3:5])[CH:3]=[O:4].[CH2:7]([O:9][C:10]([CH2:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:11])[CH3:8]>C(O)C>[CH3:5][C:2]([N:16]1[CH2:15][CH2:14][N:13]([CH2:12][C:10]([O:9][CH2:7][CH3:8])=[O:11])[CH2:18][CH2:17]1)([CH3:6])[CH:3]=[O:4]

Participants

4

Reactant 2

HCID 207112Ethyl piperazine-1-acetateHCID 5783772-Bromo-2-methylpropanal

Product 1

HCID 54505093Ethyl [4-(1,1-Dimethyl-2-oxo-ethyl)-piperazin-1-yl]-acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 100 g 2-bromo-2-methyl-propionaldehyde in 20 ml of ethanol is added dropwise to a mixture of 25.0 g N-[(ethoxycarbonyl)methyl]-piperazine in 80 ml of ethanol at room temperature. The resulting mixture is stirred for 72 hours, concentrated in vacuo, and submitted directly to column chromatography on silica gel with methylene chloride/methanol (95:5 to 80:20) to give the title compound as a yellow oil. Yield: 10.0 g (62% of theory), Rf value: 0.60 (silica gel, methylene chloride/methanol=9:1) Mass spectrum (ESI*): m/z=241 [M−H]*

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7aac4ede79e4ac4a95b142d6413c3ba
Source dataset
uspto-grants-2005_12
Patent number
US06972288B1

Reaction notes

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