Ethanol → Ethyl 4-decylpiperazine-1-carboxylate

HRID 259066Notes

Reaction equation

HRID 259066 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])(=O)=O.[CH2:16]([O:18][C:19]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)=[O:20])[CH3:17].C(O)C.C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)C>[CH2:16]([O:18][C:19]([N:21]1[CH2:22][CH2:23][N:24]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:25][CH2:26]1)=[O:20])[CH3:17]

Participants

7

Reactant 4

HCID 702EthanolHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 11430Potassium CarbonateHCID 5235508Decyl methanesulfonate

Product 1

HCID 228932Ethyl 4-decylpiperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

77.3 Grams of decyl methylsulfonate, 44.64 grams of 1-ethoxycarbonylpiperazine, 500 ml. of ethanol, and 39 grams of potassium carbonate are combined and refluxed for approximately 44 hours under a nitrogen atmosphere. After cooling to room temperature the residue is dissolved in a mixture of water and ethyl ether. The organic layer is separated, washed three times with portions of water and dried over anhydrous sodium sulfate. The solvents are removed under reduced pressure to give 1-ethoxycarbonyl-4-decylpiperazine.

Workup

  1. temperaturerefluxed for approximately 44 hours under a nitrogen atmosphere
  2. customThe organic layer is separated
  3. washwashed three times with portions of water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvents are removed under reduced pressure

Sources & evidence

ORD record
ord-2ab7a268626c4c259e68ae53ac0c746c
Source dataset
uspto-grants-1977_07
Patent number
US04036828

Reaction notes

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