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

HRID 916441Notes

Reaction equation

HRID 916441 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]#[CH:9].[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>CC(C)=O>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([CH2:9][C:8]#[CH:7])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

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

Product 1

HCID 11287538tert-Butyl 4-(prop-2-yn-1-yl)piperazine-1-carboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (1.04 g, 7.5 mmol) and propargyl bromide (654 mg, 5.5 mmol) were added to a solution of tert-butyl-1-piperazinecarboxylate (931 mg, 5.0 mmol) in acetone (5 ml). The reaction mixture was heated at 60° C. for 1 hour, and then filtered to remove the inorganics. The solvent was removed under vacuum to give a crude product which was purified by column chromatography (10-30% ethyl acetate/hexane) yielding 4-propargylpiperazine-1-carboxylic acid tert-butyl ester (894 mg, 80%).

Workup

  1. filtrationfiltered
  2. customto remove the inorganics
  3. customThe solvent was removed under vacuum
  4. customto give a crude product which
  5. customwas purified by column chromatography (10-30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3f80c44f9795452c94b569d4db7902e1
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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