Hexane → HCID 18942236, compound

HRID 355428Notes

Reaction equation

HRID 355428 reaction equation
CCCCCC.C([Li])CCC.Br[C:13](Br)=[CH:14][C:15]1[CH:16]=[CH:17][C:18]2[N:19]([CH3:29])[C:20]3[C:25]([S:26][C:27]=2[CH:28]=1)=[CH:24][CH:23]=[CH:22][CH:21]=3.[N:31]12[CH2:38][CH2:37][CH:34]([CH2:35][CH2:36]1)[C:33](=[O:39])[CH2:32]2>O.C1COCC1>[OH:39][C:33]1([CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]3[N:19]([CH3:29])[C:20]4[C:25]([S:26][C:27]=3[CH:28]=2)=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:34]2[CH2:37][CH2:38][N:31]([CH2:36][CH2:35]2)[CH2:32]1

Participants

7

Reactant 4

HCID 8058HexaneHCID 195073-QuinuclidinoneHCID 15425737HCID 15425737, compoundHCID 178418339Butyllithium

Product 1

HCID 18942236HCID 18942236, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

In an atmosphere of argon, a hexane solution of n-butyl lithium (1.65M, 10.1 ml, 16.7 mmol) was added at -78° C. to a THF (25 ml) solution of 3-(2,2-dibromovinyl)-10-methylphenothiazine (3.13 g, 7.94 mmol), and the mixture was stirred for 1 hour and then at room temperature for 1 hour. The reaction mixture was again cooled at -78° C., and a THF (8 ml) solution of 3-quinuclidinone (1.09 g, 8.70 mmol) was added dropwise. The mixture was stirred at -78° C. for 1 hour and then with ice-cooling for 30 minutes. Water (5 ml) was added to the reaction mixture and the mixture was concentrated under a reduced pressure. A potassium carbonate aqueous solution was added and the reaction product was extracted with chloroform which was heated at about 50° C. The extract was dried over anhydrous magnesium sulfate and then concentrated under a reduced pressure. The resulting residue was recrystallized from ethanol-chloroform to give the title compound (1.75 g, 4.83 mmol, 61%) as yellow crystals.

Workup

  1. waitat room temperature for 1 hour
  2. stirringThe mixture was stirred at -78° C. for 1 hour
  3. temperaturewith ice-cooling for 30 minutes
  4. concentrationthe mixture was concentrated under a reduced pressure
  5. additionA potassium carbonate aqueous solution was added
  6. extractionthe reaction product was extracted with chloroform which
  7. temperaturewas heated at about 50° C
  8. dry with materialThe extract was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under a reduced pressure
  10. customThe resulting residue was recrystallized from ethanol-chloroform

Sources & evidence

ORD record
ord-8904588df5254ce4a2f8b5b87aaf23a3
Source dataset
uspto-grants-1998_11
Patent number
US05830902

Reaction notes

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