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

HRID 1738794Notes

Reaction equation

HRID 1738794 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[CH3:5][N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1>C1(C)C=CC=CC=1>[CH3:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:1][C:2]#[CH:3])[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 7842Propargyl bromideHCID 531671-Methylpiperazine

Product 1

HCID 135140911-Methyl-4-(prop-2-yn-1-yl)piperazine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

11.1 ml (0.10 mol) of an 80% strength 2-propynyl bromide solution in toluene were added to a solution of 22.2 ml (0.20 mol) of N-methyl-piperazine in 100 ml of toluene while cooling in ice. After 30 minutes under reflux, the resulting N-methylpiperazine hydrobromide was filtered off with suction and washed with toluene, and the filtrate was washed twice each with 15% strength sodium hydroxide solution and saturated sodium chloride solution, concentrated and distilled in vacuo.

Workup

  1. temperaturewhile cooling in ice
  2. temperatureAfter 30 minutes under reflux
  3. filtrationthe resulting N-methylpiperazine hydrobromide was filtered off with suction
  4. washwashed with toluene
  5. washthe filtrate was washed twice each with 15% strength sodium hydroxide solution and saturated sodium chloride solution
  6. concentrationconcentrated
  7. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-1335bf89f8d14428b872dc63334614b1
Source dataset
uspto-grants-1999_10
Patent number
US05965555

Reaction notes

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