p-Bromochlorobenzene → HCID 69755312, compound

HRID 2416650Notes

Reaction equation

HRID 2416650 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1.[CH3:9][C@H:10]1[CH2:15][NH:14][CH2:13][C@@H:12]([CH3:16])[NH:11]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([N:14]2[CH2:13][C@H:12]([CH3:16])[NH:11][C@H:10]([CH3:9])[CH2:15]2)=[CH:3][CH:4]=1

Participants

7

Reactant 3

HCID 7806p-BromochlorobenzeneHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 23676156Sodium t-butoxide

Product 1

HCID 69755312HCID 69755312, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromochlorobenzene (1.0 g), cis-2,6-dimethylpiperazine (716 mg), sodium tert-butoxide (728 mg), (S)-(−)-BINAP (97.6 mg), and tris(dibenzylideneacetone)dipalladium(0) (71.6 mg) in anhydrous toluene (50 ml) was heated at 100° C. under a nitrogen atmosphere for 3 hours. The dark colored reaction mixture was filtered through celite and the celite was washed with chloroform. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (chloroform-methanol 60:1) to give the title compound as a yellow powder (1.15 g).

Workup

  1. filtrationThe dark colored reaction mixture was filtered through celite
  2. washthe celite was washed with chloroform
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by silica gel column chromatography (chloroform-methanol 60:1)

Sources & evidence

ORD record
ord-ae56aa3ae13c416fbb34a53a7ba322b6
Source dataset
uspto-grants-2004_11
Patent number
US06825200B1

Reaction notes

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