Piperazine → 1-(4-Cyclohexylphenyl)piperazine

HRID 390004

Reaction equation

HRID 390004 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.CC(C)([O-])C.[Na+]>CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[CH:8]1([C:5]2[CH:6]=[CH:7][C:2]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[CH:3][CH:4]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 907181-Bromo-4-cyclohexylbenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 27579961-(4-Cyclohexylphenyl)piperazine

Reagents, catalysts & solvents 1

HCID 178424406HCID 178424406, compoundCatalyst

Procedure

A target compound (2.01 g, 8.224 mmol, 45.7%) was yielded in the same manner as Reference Example 10 by reacting 1-bromo-4-cyclohexylbenzene (3.34 mL, 18 mmol) with piperazine (2.01 g, 23.4 mmol), sodium t-butoxide (2.51 g, 26.1 mmol) and dichlorobis(tri-o-tolylphosphine)palladium(II) (424.4 mg, 0.54 mmol) and purifying by separation through column chromatography (CH2Cl2/MeOH, 1:1).

Workup

  1. custompurifying by separation through column chromatography (CH2Cl2/MeOH, 1:1)

Sources & evidence

ORD record
ord-a6956ce0a8d04c79bd00f551e8a34bc6
Source dataset
uspto-grants-2013_02
Patent number
US08383631B2

Linked notes

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