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

HRID 1985625Notes

Reaction equation

HRID 1985625 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Na+].[Na+].Br[CH2:21][C:22]#[CH:23]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:23][C:22]#[CH:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 10340Sodium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 11287538tert-Butyl 4-(prop-2-yn-1-yl)piperazine-1-carboxylateYield 74.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To the degassed solution of piperazine-1-carboxylic acid tert-butyl ester (0.5 g, 2.69 mmol) in acetonitrile (5 mL) was added Na2CO3 (0.854 g, 8.05 mmol) and mixture was stirred for 20 min. The suspension was heated to 50° C. and 3-bromo-propyne (448.65 μl, 4.03 mmol) was added. The solvent was evaporated and the residue was extracted with EtOAc and water. Organic layer was washed with NaCl and NaHCO3 (2×20 ml), dried over K2CO3 and evaporated in vacuum yielding 0.45 g of the title product as yellowish oil.

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue was extracted with EtOAc and water
  3. washOrganic layer was washed with NaCl and NaHCO3 (2×20 ml)
  4. dry with materialdried over K2CO3
  5. customevaporated in vacuum

Sources & evidence

ORD record
ord-005433dca4ca466db46700003881c46c
Source dataset
uspto-grants-2009_06
Patent number
US07547679B2

Reaction notes

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