1-Tert-butylpiperazine → 1-Phenylpiperazine

HRID 2297590Notes

Reaction equation

HRID 2297590 reaction equation
C(O[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1Br)CCC.C([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)(C)(C)C.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[C:6]1([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 35305721-Tert-butylpiperazineHCID 190081261-Bromo-2-butoxybenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 70961-PhenylpiperazineYield 157.1%

Reagents, catalysts & solvents 2

HCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolvent

Procedure

Part A: To a solution of n-butyloxybromobenzene (5.00 g, 21.82 mmol) in toluene (50 mL) was added tert-butyl piperazine (4.88 g, 26.18 mmol) and sodium tert-butoxide (2.94 g, 30.55 mmol). After stirring at ambient temperature for several minutes, BINAP (0.408 g, 0.655 mmol) and tris(dibenzyldeneacetone)-dipallidium (0) (0.200 g, 0.218 mmol) were added. The resulting mixture was heated to eighty degrees Celsius for 21 hours. After cooling to ambient temperature, the reaction mixture was filtered through a pad of Celite®, washing with diethyl ether and dichloromethane. Chromatography (on silica, ethyl acetate/hexanes) provided the phenyl-piperazine as a tan solid (5.56 g, 76%).

Workup

  1. temperatureThe resulting mixture was heated to eighty degrees Celsius for 21 hours
  2. temperatureAfter cooling to ambient temperature
  3. filtrationthe reaction mixture was filtered through a pad of Celite®
  4. washwashing with diethyl ether and dichloromethane

Sources & evidence

ORD record
ord-57d6173298034604bd9735ba369e20f5
Source dataset
uspto-grants-2002_12
Patent number
US06492367B1

Reaction notes

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