Water → 1-Oleoylpiperazine

HRID 892889Notes

Reaction equation

HRID 892889 reaction equation
[CH2:1](Cl)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[NH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.[OH2:26]>C(Cl)Cl>[C:1]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)(=[O:26])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 4837PiperazineHCID 53677849-Octadecene, 1-chloro-

Product 1

HCID 677939691-OleoylpiperazineYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3.0 g of oleyl chloride in 10 mg of methylene chloride was added portion-wise to a solution of 4.3 g of piperazine in 30 ml of methylene chloride with stirring under ice cooling. After stirring the mixture in situ for additional 2 hours, 10 ml of water was added to the reaction mixture to separate the organic layer. The organic layer was further washed with water and dried over anhydrous sodium sulfate, followed by removal of the solvent by evaporation. The residue obtained was purified by silica gel column chromatography to obtain 2.68 g of the objective compound (yield: 76%).

Workup

  1. stirringAfter stirring the mixture in situ for additional 2 hours
  2. customto separate the organic layer
  3. washThe organic layer was further washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customfollowed by removal of the solvent by evaporation
  6. customThe residue obtained
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e9f128aba7b84a5bb177cc6ad75977e9
Source dataset
uspto-grants-1992_06
Patent number
US05120738

Reaction notes

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