Propargyl bromide → 1-Methyl-4-(prop-2-yn-1-yl)piperazine

HRID 1403215Notes

Reaction equation

HRID 1403215 reaction equation
Br[CH2:2][C:3]#[CH:4].[CH3:5][N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:2][C:3]#[CH:4])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 531671-Methylpiperazine

Product 1

HCID 135140911-Methyl-4-(prop-2-yn-1-yl)piperazineYield 51%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 3-bromoprop-1-yne (1.70 mL, 22.5 mmol in acetone (7 mL) was added to a suspension of 1-methylpiperazine (3.77 mL, 33.7 mmol) and K2CO3 (4.66 g, 33.7 mmol) in acetone (40 mL) at 0° C. The mixture was stirred at room temperature for 4 h and then filtered. The filtrate was evaporated to dryness and the residue was taken up with water (80 mL) and extracted with DCM (2×20 mL). The separated organic phase was washed with brine (3×5 mL), dried over sodium sulfate and evaporated to afford the title compound as brown oil (1.60 g, 51%).

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated to dryness
  3. extractionextracted with DCM (2×20 mL)
  4. washThe separated organic phase was washed with brine (3×5 mL)
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-f5fd91c89f6e46609417f5d6eb4a5723
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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