Pentane → HCID 12973058, compound

HRID 351334Notes

Reaction equation

HRID 351334 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.C([Li])(C)(C)C.CCCCC.[CH3:21][N:22]([CH3:36])[C:23]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]1>C1COCC1>[CH3:21][N:22]([CH3:36])[C:23]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:28][CH2:27][C:26]([C:3]2[N:2]([CH3:1])[C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)([OH:29])[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 8003PentaneHCID 117811-MethylindoleHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-oneHCID 178418306HCID 178418306, compound

Product 1

HCID 12973058HCID 12973058, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of N-methylindol (400 mg, 3.05 mmol) in dry THF (20 ml) was cooled to −5° C. under a stream of argon. Tert-butyllithium (3.65 mmol, 2.15 ml of a 1.7 molar pentane solution) was 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 (662 mg, 3.05 mmol) in dry THF (5 ml) was added dropwise at 0° C. The mixture was stirred for 15 minutes at 0° C. and then 4 hours 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=7:3) over silica gel. 318 mg 4-dimethylamino-1-(1-methyl-1H-indol-2-yl)-4-phenylcyclohexanol with a melting point of 163–165° C. were obtained.

Workup

  1. additionOnce all the substance had been added
  2. stirringThe mixture was stirred for 15 minutes at 0° C.
  3. custom4 hours
  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-6a4b2c2e193841858e64b7a7695ef537
Source dataset
uspto-grants-2007_02
Patent number
US07183436B2

Reaction notes

Loading…