Hexane → 1-(1-benzenesulfonyl-1H-indol-2-yl)-4-dimethylamino-4-phenylcyclohexanol

HRID 351336

Reaction equation

HRID 351336 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.CCCCCC.[CH3:30][N:31]([CH3:45])[C:32]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:37][CH2:36][C:35](=[O:38])[CH2:34][CH2:33]1>C1COCC1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:35]2([OH:38])[CH2:36][CH2:37][C:32]([N:31]([CH3:30])[CH3:45])([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:33][CH2:34]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 3150171-(Phenylsulfonyl)-1H-indoleHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-oneHCID 178418339Butyllithium

Product 1

HCID 129730611-(1-benzenesulfonyl-1H-indol-2-yl)-4-dimethylamino-4-phenylcyclohexanolYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1-benzenesulfonyl-1H-indol (600 mg, 2.33 mmol) in dry THF (30 ml) was cooled to −5° C. under a stream of argon. n-butyllithium (2.79 mmol, 1.75 ml of a 1.6 molar hexane solution) were added dropwise in such a way that a reaction temperature of 0° C. was not exceeded. Once all the substance had been added, the reaction mixture was stirred for 2 hours at 0° C. A solution of 4-dimethylamino-4-phenylcyclohexanone (493 mg, 2.33 mmol) in dry THF (5 ml) was added dropwise at 0° C. The mixture was stirred for 1 hour at 0° C. and then 3 days at ambient temperature. The reaction mixture was quenched with saturated ammonium chloride solution (20 ml), the organic phase was separated and the aqueous phase extracted four times with dichloromethane (20 ml). The combined organic phases were dried over sodium sulfate, filtered and the solvent removed under vacuum. Purification was carried out by flash chromatography with cyclohexane/ethylacetate (V:V=1:1) over silica gel. 232 mg 1-(1-benzenesulfonyl-1H-indol-2-yl)-4-dimethylamino-4-phenylcyclohexanol with a melting point of 173–176° C. were obtained.

Workup

  1. additionOnce all the substance had been added
  2. stirringThe mixture was stirred for 1 hour at 0° C.
  3. custom3 days
  4. customat ambient temperature
  5. customThe reaction mixture was quenched with saturated ammonium chloride solution (20 ml)
  6. customthe organic phase was separated
  7. extractionthe aqueous phase extracted four times with dichloromethane (20 ml)
  8. dry with materialThe combined organic phases were dried over sodium sulfate
  9. filtrationfiltered
  10. customthe solvent removed under vacuum
  11. customPurification

Sources & evidence

ORD record
ord-175722b7fda345c1af8504004493ea8e
Source dataset
uspto-grants-2007_02
Patent number
US07183436B2

Linked notes

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