1-Bromo-4-propylbenzene → HCID 58487948, compound

HRID 888186Notes

Reaction equation

HRID 888186 reaction equation
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.Br[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=1.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.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][C@H:2]1[NH:3][CH2:4][CH2:5][N:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)[CH2:7]1

Participants

7

Reactant 4

HCID 1363741-Bromo-4-propylbenzeneHCID 634876Binap, (A+-)-HCID 73304342-Methylpiperazine, (R)-HCID 23676156Sodium t-butoxide

Product 1

HCID 58487948HCID 58487948, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of (R)-2-methylpiperazine (3.00 g, 30.0 mmol, 1.0 eq), 1-bromo-4-propylbenzene (627 g, 31.5 mmol, 1.05 eq.), (+/−)-BINAP (747 mg, 1.2 mmol, 0.04 eq.) and sodium tert-butoxide (4.32 g, 45.0 mmol, 1.5 eq.) in toluene (70 mL) was degassed for 15 min with N2. Palladium(II) acetate (337 mg, 1.5 mmol, 0.05 eq.) was then added at once. The reaction mixture was then heated to reflux for 16 h then cooled to RT. The mixture was then filtered on a bed of cellite and washed with Et2O. The combined organic layers were then washed with H2O (3×), dried over MgSO4, filtered and evaporated to give a dark to brown oil. This residue was purified by chromatography on silicagel (DCM/MeOH 80/20) to give the title product as yellow oil (2.35 g, 36%). M+(ESI): 2192.

Workup

  1. customwas degassed for 15 min with N2
  2. temperatureThe reaction mixture was then heated
  3. temperatureto reflux for 16 h
  4. filtrationThe mixture was then filtered on a bed of cellite
  5. washwashed with Et2O
  6. washThe combined organic layers were then washed with H2O (3×)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customto give a dark to brown oil
  11. customThis residue was purified by chromatography on silicagel (DCM/MeOH 80/20)

Sources & evidence

ORD record
ord-fcd042dc7b9647f4abd39442cab42d6b
Source dataset
uspto-grants-2012_08
Patent number
US08247437B2

Reaction notes

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