Cyclohexene → 1-Nonylpiperazine

HRID 355671Notes

Reaction equation

HRID 355671 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:10][CH2:9]1)C1C=CC=CC=1.C1CCCCC=1>C(O)C.[OH-].[OH-].[Pd+2]>[CH2:14]([N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 189404201-Benzyl-4-nonylpiperazine

Product 1

HCID 27370981-Nonylpiperazine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-benzyl-4-nonylpiperazine (0.54 g, 1.80 mmol) (prepared by reacting 1-benzylpiperazine, Aldrich, with 1-bromononane, Aldrich, and NaH in DMF), palladium hydroxide on carbon (0.14 g) and cyclohexene (7 mL) in ethanol (15 mL) was heated at reflux overnight. After filtration, the filtrate was concentrated in vacuo to dryness to give 1-nonylpiperazine as an oil, 0.38 g, 100%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-5b12d43dcc414c808ffcfc4cf7b810a6
Source dataset
uspto-grants-1998_11
Patent number
US05834459

Reaction notes

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