Water → {4-[1-(1-Ethoxy-ethoxy)-2-phenylethyl]-1-thiophen-2-yl-cyclohexyl}dimethylamine

HRID 2063720

Reaction equation

HRID 2063720 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[Mg]Br.[CH3:8][N:9]([CH3:32])[C:10]1(C#N)[CH2:15][CH2:14][CH:13]([CH:16]([O:24][CH:25]([O:27][CH2:28][CH3:29])[CH3:26])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:12][CH2:11]1.O.[Cl-].[NH4+]>O1CCCC1>[CH2:28]([O:27][CH:25]([O:24][CH:16]([CH:13]1[CH2:14][CH2:15][C:10]([N:9]([CH3:32])[CH3:8])([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[CH2:11][CH2:12]1)[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH3:26])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 698102431-Dimethylamino-4-[1-(1-ethoxy-ethoxy)-2-phenylethyl]cyclohexanecarbonitrileHCID 178418438HCID 178418438, compound

Product 1

HCID 66886988{4-[1-(1-Ethoxy-ethoxy)-2-phenylethyl]-1-thiophen-2-yl-cyclohexyl}dimethylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1 M solution of 2-thienylmagnesium 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 water and saturated ammonium chloride solution (10 ml of each) were then 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-19de3ed48a564ae88aaf8370da9857a1
Source dataset
uspto-grants-2012_10
Patent number
US08288406B2

Linked notes

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