Propargyl bromide → Tert-butyl 4-(pent-4-yn-1-yl)piperazine-1-carboxylate

HRID 1740387Notes

Reaction equation

HRID 1740387 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17]O)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH2:19](Br)[C:20]#[CH:21]>O1CCCC1>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:21][C:20]#[CH:19])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 735736Tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylate

Product 1

HCID 21838636Tert-butyl 4-(pent-4-yn-1-yl)piperazine-1-carboxylateYield 108.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a refluxing solution of 1.67 g of sodium hydride in 20 mL of tetrahydrofuran was added dropwise a solution of 9.00 g of 1-tert-butoxycarbonyl-4-(2-hydroxyethyl)piperazine in 15 mL of tetrahydrofuran and then 5.63 g of propargyl bromide was added dropwise to the resultant mixture. After completion of the reaction, the mixture was concentrated, poured into ice-water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and evaporated to give 10.70 g of the title compound.

Workup

  1. customAfter completion of the reaction
  2. concentrationthe mixture was concentrated
  3. additionpoured into ice-water
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-ad4c5a0c0c834327ad87fcd91896f013
Source dataset
uspto-grants-1999_10
Patent number
US05969138

Reaction notes

Loading…