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

HRID 1677745Notes

Reaction equation

HRID 1677745 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 (6.27 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 brown oil. This residue was purified by chromatography on silica gel (DCM/MeOH 80/20) to give the title product as yellow oil (2.35 g, 36%). M+(ESI): 219.2.

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 brown oil
  11. customThis residue was purified by chromatography on silica gel (DCM/MeOH 80/20)

Sources & evidence

ORD record
ord-4d4e54382b3546d7bd213a8aac4c9b59
Source dataset
uspto-grants-2011_08
Patent number
US08008302B2

Reaction notes

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