1-Methylpiperazine → 1-Ethyl-4-(4-pentyn-1-yl)piperazine

HRID 417861Notes

Reaction equation

HRID 417861 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]#[CH:10])(=O)=O.[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[C:18]([O-])(O)=O.[Na+]>ClCCCl>[CH2:11]([N:12]1[CH2:17][CH2:16][N:15]([CH2:6][CH2:7][CH2:8][C:9]#[CH:10])[CH2:14][CH2:13]1)[CH3:18]

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 12476209Pent-4-yn-1-yl methanesulfonate

Product 1

HCID 866082201-Ethyl-4-(4-pentyn-1-yl)piperazine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of pent-4-ynyl methanesulfonate (849 mg) and N-methyl piperazine (665 μL) was heated to 80° C. for 3 h, diluted with 1,2-dichloroethane (5 mL) and heated to 70° C. for 18 h. Saturated aq. NaHCO3 was added (10 mL) and the mixture was extracted with DCM (1×40 mL), dried over Na2SO4, and concentrated to afford 0.56 g of 1-ethyl-4-(pent-4-ynyl)piperazine.

Workup

  1. temperatureheated to 70° C. for 18 h
  2. extractionthe mixture was extracted with DCM (1×40 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d79befbc72c44742983260f1a91c0fdd
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

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