Ammonium Chloride → Cyclohexanol, 4-(dimethylamino)-4-phenyl-1-(2-phenylethyl)-

HRID 351330Notes

Reaction equation

HRID 351330 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.[CH2:17]([Mg]Cl)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:8][CH2:7][C:6]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([OH:9])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-oneHCID 178418865HCID 178418865, compound

Product 1

HCID 10109140Cyclohexanol, 4-(dimethylamino)-4-phenyl-1-(2-phenylethyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.83 g 4-dimethylamino-4-phenylcyclohexanone dissolved in 10 ml tetrahydrofuran were added dropwise to 21 ml 1.0 molar phenethyl magnesium chloride solution in tetrahydrofuran and the mixture was stirred overnight at ambient temperature. To work up the mixture with ice cooling, 15 ml ammonium chloride solution (20% by weight) were added, the mixture was extracted three times with 15 ml ethylacetate in each case, the extracts were combined, dried over sodium sulfate, filtered, concentrated and substantially freed of solvent residues under vacuum. The crude 4-dimethylamino-1-phenethyl-4-phenylcyclohexanol (5.75 g) obtained was obtained as a brown oil which was chromatographed with diethylether/hexane (V:V=1:1) over silica gel. 1.71 g 4-dimethylamino-1-phenethyl-4-phenylcylcohexanol were obtained in the form of yellow crystals which were dissolved in 6.8 ml 2-butanone and converted by reaction with 26 μl water and 366 μl chlorotrimethylsilane, stirring overnight with subsequent filtration into 838 mg of the corresponding hydrochloride.

Workup

  1. additionwere added
  2. extractionthe mixture was extracted three times with 15 ml ethylacetate in each case
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude 4-dimethylamino-1-phenethyl-4-phenylcyclohexanol (5.75 g) obtained
  7. customwas obtained as a brown oil which
  8. customwas chromatographed with diethylether/hexane (V:V=1:1) over silica gel

Sources & evidence

ORD record
ord-3c707ef1766c4444b2e8eec663b6272a
Source dataset
uspto-grants-2007_02
Patent number
US07183436B2

Reaction notes

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