Water → HCID 69811611, compound

HRID 2063724Notes

Reaction equation

HRID 2063724 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([Mg]Br)[CH:6]=[CH:7][CH:8]=1.[CH3:11][N:12]([CH3:35])[C:13]1(C#N)[CH2:18][CH2:17][CH:16]([CH:19]([O:27][CH:28]([O:30][CH2:31][CH3:32])[CH3:29])[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:15][CH2:14]1.O.[Cl-].[NH4+]>O1CCCC1>[CH2:31]([O:30][CH:28]([O:27][CH:19]([CH:16]1[CH2:17][CH2:18][C:13]([N:12]([CH3:35])[CH3:11])([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:14][CH2:15]1)[CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH3:29])[CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 698102431-Dimethylamino-4-[1-(1-ethoxy-ethoxy)-2-phenylethyl]cyclohexanecarbonitrileHCID 178490745HCID 178490745, compound

Product 1

HCID 69811611HCID 69811611, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1 M solution of 3-methoxyphenylmagnesium bromide in tetrahydrofuran (9.25 ml, 9.25 mmol) was added dropwise to a solution of 1-dimethylamino-4-[1-(1-ethoxy-ethoxy)-2-phenylethyl]cyclohexanecarbonitrile (1.06 g, 3.1 mmol) in tetrahydrofuran (15 ml), while cooling with ice and under an argon atmosphere. The mixture was stirred at room temperature for 48 h and thereafter water and saturated ammonium chloride solution (10 ml of each) were added. The phases were separated and the aqueous phase was extracted with diethyl ether (3×10 ml). The combined organic phases were dried with sodium sulfate and concentrated i. vac.

Workup

  1. temperaturewhile cooling with ice and under an argon atmosphere
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with diethyl ether (3×10 ml)
  4. dry with materialThe combined organic phases were dried with sodium sulfate
  5. concentrationconcentrated i

Sources & evidence

ORD record
ord-c2f3f223e4414f83a7715a72e3a49a6c
Source dataset
uspto-grants-2012_10
Patent number
US08288406B2

Reaction notes

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