Water → {4-[1-(1-Ethoxy-ethoxy)-2-phenoxyethyl]-1-phenylcyclohexyl}dimethylamine

HRID 2063742Notes

Reaction equation

HRID 2063742 reaction equation
[CH3:1][N:2]([CH3:26])[C:3]1([C:24]#N)[CH2:8][CH2:7][CH:6]([CH:9]([O:18][CH:19]([O:21][CH2:22][CH3:23])[CH3:20])[CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:5][CH2:4]1.[C:27]1([Mg]Cl)[CH:32]=[CH:31]C=[CH:29][CH:28]=1.[Cl-].[NH4+].O>O1CCCC1>[CH2:22]([O:21][CH:19]([O:18][CH:9]([CH:6]1[CH2:7][CH2:8][C:3]([N:2]([CH3:26])[CH3:1])([C:24]2[CH:31]=[CH:32][CH:27]=[CH:28][CH:29]=2)[CH2:4][CH2:5]1)[CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:20])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 668865171-Dimethylamino-4-[1-(1-ethoxy-ethoxy)-2-phenoxyethyl]cyclohexanecarbonitrileHCID 178478979HCID 178478979, compound

Product 1

HCID 66886952{4-[1-(1-Ethoxy-ethoxy)-2-phenoxyethyl]-1-phenylcyclohexyl}dimethylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-dimethylamino-4-[1-(1-ethoxy-ethoxy)-2-phenoxyethyl]cyclohexanecarbonitrile (871 mg, 2.4 mmol) in anhydrous tetrahydrofuran (15 ml) was added dropwise to a 2 M solution of phenylmagnesium chloride in tetrahydrofuran (3.6 ml, 7.3 mmol), while cooling with ice. The mixture was stirred at room temperature overnight and saturated ammonium chloride solution and water (5 ml of each) were then added. The phases were separated and the aqueous phase was extracted with diethyl ether (3×20 ml). The combined organic phases were dried with sodium sulfate and concentrated in vacuo.

Workup

  1. temperaturewhile cooling with ice
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with diethyl ether (3×20 ml)
  4. dry with materialThe combined organic phases were dried with sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-20ebb34ddcac46439cf4026fa35858d1
Source dataset
uspto-grants-2012_10
Patent number
US08288406B2

Reaction notes

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