Methyl vinyl ketone → HCID 23081416, compound

HRID 856016Notes

Reaction equation

HRID 856016 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH:14]([C:16]([CH3:18])=[O:17])=[CH2:15]>C1COCC1>[O:17]=[C:16]([CH3:18])[CH2:14][CH2:15][N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 23081416HCID 23081416, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tert-butyl piperazine-1-carboxylate (6 g, 32.3 mmol) in THF (50 ml) was gradually added dropwise to a solution of methyl vinyl ketone (2.3 g, 32.9 mmol) in THF (25 ml) while cooling in an ice-bath, and the mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1) to afford tert-butyl 4-(3-oxobutyl)piperazine-1-carboxylate (7.2 g, yield 87%)as a pale yellow oil.

Workup

  1. temperaturewhile cooling in an ice-bath
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1)

Sources & evidence

ORD record
ord-72d16e7d13404e3cb40a6c4089925b85
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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