Hexane → HCID 23288937, compound

HRID 368850Notes

Reaction equation

HRID 368850 reaction equation
C1(PC2C=CC=CC=2)C=CC=CC=1.C([Li])CCC.CCCCCC.[ClH:25].Cl.[CH:27]1([CH2:36][CH2:37][N:38]2[CH2:43][CH2:42][N:41]([C:44]3[CH:49]=[CH:48][C:47]([O:50]C)=[CH:46][CH:45]=3)[CH2:40][CH2:39]2)[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][CH2:28]1>C1COCC1>[ClH:25].[ClH:25].[CH:27]1([CH2:36][CH2:37][N:38]2[CH2:43][CH2:42][N:41]([C:44]3[CH:45]=[CH:46][C:47]([OH:50])=[CH:48][CH:49]=3)[CH2:40][CH2:39]2)[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 70017DiphenylphosphineHCID 23288871HCID 23288871, compoundHCID 178418339Butyllithium

Product 1

HCID 23288937HCID 23288937, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diphenylphosphine (8.7 ml, 50 mmol) in THF (60 ml) is cooled to 0° under a nitrogen atmosphere and treated with n-butyllithium in hexane (1.6 M, 31.3 ml, 50 mmol). After stirring for 10 min, a solution of 4-[2-(indan-1-yl)ethyl]-1-(4-methoxyphenyl)piperazine (CXII, EXAMPLE 70, 6.73 g, 20 mmol) in THF (20 ml) is added. The mixture is refluxed for 24 hr, quenched with water and extracted with ethyl acetate (2×800 ml). The organic phase is washed with water, saline, dried (magnesium sulfate), filtered and concentrated under reduced pressure. The concentrate is purified by liquid chromatography on silica gel 60 (230-400 mesh, 400 g), eluting with hexane/acetone (2/1). The appropriate fractions homogeneous by TLC are combined and concentrated to give the free base of the title compound. This free base is converted into the hydrochloric acid salt and recrystallized from ethyl acetate/methanol to give the title compound, mp 215-216°, NMR (DMSO-d6, TMS) 7.30-6.68 and 3.68-1.60 δ.

Workup

  1. temperatureThe mixture is refluxed for 24 hr
  2. customquenched with water
  3. extractionextracted with ethyl acetate (2×800 ml)
  4. washThe organic phase is washed with water, saline
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe concentrate is purified by liquid chromatography on silica gel 60 (230-400 mesh, 400 g)
  9. washeluting with hexane/acetone (2/1)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-3665b149f2e143a09c209c8a73e22544
Source dataset
uspto-grants-2000_10
Patent number
US06133446

Reaction notes

Loading…