Water → HCID 12831592, compound

HRID 1446813Notes

Reaction equation

HRID 1446813 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]2[C:13](Br)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.C([Li])CCC.[CH3:20][N:21]([CH3:29])[CH:22]1[CH2:27][CH2:26][C:25](=[O:28])[CH2:24][CH2:23]1.O>CCCCCC.O1CCCC1>[C:4]1([CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[C:25]2([OH:28])[CH2:26][CH2:27][CH:22]([N:21]([CH3:29])[CH3:20])[CH2:23][CH2:24]2)[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 130611-Benzyl-2-bromobenzeneHCID 103745454-(Dimethylamino)cyclohexan-1-oneHCID 178418339Butyllithium2×

Product 1

HCID 12831592HCID 12831592, compoundYield 30.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To 24.7 g of 2-bromodiphenylmethane and 100 ml of dry tetrahydrofuran (THF, hereinafter) is added 55 ml of 2.4 molar solution of n-butyllithium in hexane dropwise with stirring at -40° to 50° C. under a dry nitrogen atmosphere. The resultant solution is stirred one hour after addition of the n-butyllithium is completed. A solution of 15.5 g 4-dimethylaminocyclohexanone in 50 ml of dry THF is added dropwise with stirring while maintaining the temperature below -40° C. The resultant solution is stirred at -40°0 to -50° C. for two hours after addition of the ketone is completed and further stirred under N2 atmosphere overnight (16 hours) at room temperature. The solution is cooled to 0° C. and 350 ml of water and 400 ml of hexane are added thereto. The aqueous phase of the resultant mixture is removed and the product crystallized out of the organic phase. After filtration (washing the filter cake with hexane) the organic phase is washed three times with 100°ml portions of water and cooled overnight. A second crop is obtained, combined with the first crop and recrystallized from 50 ml of toluene to yield 9.46 g (30.6% yield) of 1-[2-(phenylmethyl)phenyl]-4-dimethylaminocyclohexanol, m.p. 140°-141° C.

Workup

  1. stirringwith stirring
  2. temperaturewhile maintaining the temperature below -40° C
  3. stirringfurther stirred under N2 atmosphere overnight (16 hours) at room temperature
  4. customThe aqueous phase of the resultant mixture is removed
  5. customthe product crystallized out of the organic phase
  6. filtrationAfter filtration (
  7. washwashing the filter cake with hexane) the organic phase
  8. washis washed three times with 100°ml portions of water
  9. temperaturecooled overnight
  10. customA second crop is obtained
  11. customrecrystallized from 50 ml of toluene

Sources & evidence

ORD record
ord-dce2096c8e344001bf05faf40dc3a884
Source dataset
uspto-grants-1982_02
Patent number
US04313959

Reaction notes

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