Sodium Hydroxide → (4-Dimethylaminomethyl-1,4-diphenyl-cyclohexyl)-dimethylamine

HRID 76931Notes

Reaction equation

HRID 76931 reaction equation
[C:1]1([Mg]Cl)[CH:6]=[CH:5]C=[CH:3][CH:2]=1.[CH3:9][N:10]([CH3:29])[C:11]1([C:27]#N)[CH2:16][CH2:15][C:14]([CH2:23][N:24]([CH3:26])[CH3:25])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][CH2:12]1.[NH4+].[Cl-].[OH-].[Na+]>O.C1COCC1>[CH3:25][N:24]([CH2:23][C:14]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:13][CH2:12][C:11]([N:10]([CH3:9])[CH3:29])([C:27]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH2:16][CH2:15]1)[CH3:26]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 68306788HCID 68306788, compoundHCID 178478979HCID 178478979, compound

Product 1

HCID 44252391(4-Dimethylaminomethyl-1,4-diphenyl-cyclohexyl)-dimethylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2M phenylmagnesium chloride solution in THF (3.5 mL, 7.0 mmol) was slowly added in drops to a solution of the title compound of step 7 (1.00 g, 3.5 mmol) in abs. THF (10 mL) in a nitrogen atmosphere and with ice cooling at 10° C. The solution was stirred for 20 h at RT. Then 20% NH4Cl solution (5 mL) and water (2 mL) were added and the solution was extracted with ether (3×5 mL). The combined organic phases were washed with water (2 mL) and saturated NaCl solution (2 mL), dried over Na2SO4 and concentrated to low volume in a vacuum. By flash chromatography of the residue with chloroform/methanol (20:1) a salt of the product was obtained that was released with 1N NaOH, extracted with chloroform, dried over Na2SO4, and the solvent removed from it in a vacuum.

Workup

  1. customat 10° C
  2. extractionthe solution was extracted with ether (3×5 mL)
  3. washThe combined organic phases were washed with water (2 mL) and saturated NaCl solution (2 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to low volume in a vacuum
  6. customBy flash chromatography of the residue with chloroform/methanol (20:1) a salt of the product was obtained
  7. extractionextracted with chloroform
  8. dry with materialdried over Na2SO4
  9. customthe solvent removed from it in a vacuum

Sources & evidence

ORD record
ord-f6af45f82e15474c8a9ddd95cb7833ff
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

Loading…