Water → tert-Butyl 4-(prop-2-yn-1-yl)piperazine-1-carboxylate

HRID 1749941Notes

Reaction equation

HRID 1749941 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH2:1]([N:15]1[CH2:14][CH2:13][N:12]([C:10]([O:9][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:11])[CH2:17][CH2:16]1)[C:2]#[CH:3]

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 11287538tert-Butyl 4-(prop-2-yn-1-yl)piperazine-1-carboxylateYield 83.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A solution of propargyl bromide (0.766 g, 6.44 mmol) in acetonitrile (25 mL) was added with 1-tert-butoxycarbonylpiperazine (1.00 g, 5.37 mmol) and potassium carbonate (1.11 g, 8.03 mmol), and the mixture was stirred at 60° C. for 4 hours. The reaction mixture was added with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain tert-butyl 4-(prop-2-ynyl)piperazine-1-carboxylate (1.01 g, 83%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1bcd7fb0f58d443e8f480066e71fe3ee
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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