1-Decanol → Ethyl 4-decylpiperazine-1-carboxylate

HRID 1707623Notes

Reaction equation

HRID 1707623 reaction equation
[N:1]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CS(O[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])(=O)=O.C(O)CCCCCCCCC.CS(Cl)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CCO>[CH2:17]([N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2][CH2:3]1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 5

HCID 81741-DecanolHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 5235508Decyl methanesulfonate

Product 1

HCID 228932Ethyl 4-decylpiperazine-1-carboxylateYield 63.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-piperazinecarboxylate (77.3 g, 0.28 mole), 1-decanol methanesulfonate (77.3 g, 0.28 mole) from the condensation of 1-decanol with methane sulfonyl chloride, K2CO3 (39.0 g, 0.28 mole), and 500 mL of EtOH were combined and refluxed for 2 days under N2. After cooling to room temperature, the reaction was partitioned between water and Et2O. The organic layer was separated, washed 3 times with water, dried over Na2SO4 and stripped of all solvent under reduced pressure to yield the crude product oil. Chromatographic purification of the crude oil gave 53.4 g of ethyl 4-decyl-1-piperazinecarboxylate.

Workup

  1. temperaturerefluxed for 2 days under N2
  2. customthe reaction was partitioned between water and Et2O
  3. customThe organic layer was separated
  4. washwashed 3 times with water
  5. dry with materialdried over Na2SO4
  6. customto yield the crude product oil
  7. customChromatographic purification of the crude oil

Sources & evidence

ORD record
ord-da1018476a9342e09a2c152fb4e973fb
Source dataset
uspto-grants-1994_10
Patent number
US05354747

Reaction notes

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