1-Chlorodecane → Piperazine, 1-decyl-4-methyl-

HRID 1438836Notes

Reaction equation

HRID 1438836 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH2:8](Cl)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[OH-].[Na+]>O.C(O)C(C)C>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 138481-ChlorodecaneHCID 14798Sodium HydroxideHCID 531671-Methylpiperazine

Product 1

HCID 11776460Piperazine, 1-decyl-4-methyl-Yield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6560IsobutanolSolvent

Conditions

Temperature
150 °C

Procedure

100 g (1 mole) of 1-methyl-piperazine and 176.5 g (1 mole) of decyl chloride were heated under reflux, at an external temperature of 150° C, until the reaction mixture had ceased boiling. After cooling, the solid product was extracted by shaking with a mixture with 40 g (1 mole) of sodium hydroxide in 500 ml of water and 500 ml of isobutanol. The organic phase was separated off and concentrated, and the residue was extracted with petroleum ether. After evaporating the petroleum ether solution, 180 g (75% of theory) of 1-methyl-4-decyl-piperazine were obtained in a form which was pure according to thin layer chromatography.

Workup

  1. temperatureAfter cooling
  2. extractionthe solid product was extracted
  3. customThe organic phase was separated off
  4. concentrationconcentrated
  5. extractionthe residue was extracted with petroleum ether
  6. customAfter evaporating the petroleum ether solution

Sources & evidence

ORD record
ord-6561f23eefa645af89901cbd6e127488
Source dataset
uspto-grants-1977_11
Patent number
US04057413

Reaction notes

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