Diisopropylamine → HCID 53760246, compound

HRID 355429Notes

Reaction equation

HRID 355429 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.C([N-]C(C)C)(C)C.[Li+].[C:21]([C:24]1[CH:37]=[CH:36][C:35]2[S:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([CH3:38])[C:26]=2[CH:25]=1)(=[O:23])[CH3:22].[N:39]12[CH2:46][CH2:45][CH:42]([CH2:43][CH2:44]1)[C:41](=[O:47])[CH2:40]2>O.C1COCC1.CCCCCC>[CH3:38][N:27]1[C:26]2[CH:25]=[C:24]([C:21]([CH2:22][C:41]3([OH:47])[CH:42]4[CH2:45][CH2:46][N:39]([CH2:44][CH2:43]4)[CH2:40]3)=[O:23])[CH:37]=[CH:36][C:35]=2[S:34][C:33]2[C:28]1=[CH:29][CH:30]=[CH:31][CH:32]=2

Participants

9

Reactant 5

HCID 7912DiisopropylamineHCID 195073-QuinuclidinoneHCID 914011-(10-Methyl-10H-phenothiazin-2-yl)ethan-1-oneHCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

Product 1

HCID 53760246HCID 53760246, compoundYield 53.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

In an atmosphere of argon, a hexane solution of n-butyl lithium (1.71M, 4.94 ml, 8.45 mmol) was added at -78° C. to a THF (8 ml) solution of diisopropylamine (1.23 ml, 8.8 mmol), and the mixture was stirred for 40 minutes. To the solution of the resulting lithium diisopropylamide was added a THF (8 ml) solution of 2-acetyl-10-methylphenothiazine (1.96 g, 7.68 mmol), and the mixture was stirred for 1 hour. A THF (8 ml) solution of 3-quinuclidinone (951 mg, 7.60 mmol) was added, the mixture was stirred at -78° C. for 30 minutes and then with ice-cooling for 15 minutes. Water was added to the reaction mixture and the reaction product was extracted with chloroform. The extract was washed with saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; 29% aqueous ammonia:methanol:chloroform=1:10:90) to give the title compound (1.55 g, 4.07 mmol, 53%) as yellow foam.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. stirringthe mixture was stirred at -78° C. for 30 minutes
  3. temperaturewith ice-cooling for 15 minutes
  4. extractionthe reaction product was extracted with chloroform
  5. washThe extract was washed with saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under a reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (eluent; 29% aqueous ammonia:methanol:chloroform=1:10:90)

Sources & evidence

ORD record
ord-296518a0ef204d4d8039c5a0fa050d33
Source dataset
uspto-grants-1998_11
Patent number
US05830902

Reaction notes

Loading…