Toluene → 1-Bromo-12-(4-phenylpiperazinyl)dodecane

HRID 36762

Reaction equation

HRID 36762 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Br:14].[C:15]1([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.C1(C)C=CC=CC=1>C(OCC)(=O)C>[Br:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:24]1[CH2:25][CH2:26][N:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 187661,12-Dibromododecane

Product 1

HCID 199377541-Bromo-12-(4-phenylpiperazinyl)dodecaneYield 50.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6.56 g of 1,12-dibromododecane, 3.24 g of N-phenylpiperazine, 2.53 g of triethylamine, and 50 ml of toluene was heated under reflux for 2 hours. To the reaction mixture was added 100 ml of ethyl acetate, and the mixture was washed successively with water and a saturated sodium chloride aqueous solution, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to column chromatography using a 1:2 mixture of ethyl acetate and hexane as a developing solvent to yield 4.1 g of 1-bromo-12-(4-phenylpiperazinyl)dodecane (m.p.=26.0°-28.0° C.).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. washthe mixture was washed successively with water
  4. dry with materiala saturated sodium chloride aqueous solution, and dried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additiona 1:2 mixture of ethyl acetate and hexane as a developing solvent

Sources & evidence

ORD record
ord-fa353175c04246a7aadabf201b983965
Source dataset
uspto-grants-1995_05
Patent number
US05416212

Linked notes

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