Hydrochloric Acid → 1-Dimethylamino-4-[1-(1-ethoxy-ethoxy)-2-phenoxyethyl]cyclohexanecarbonitrile
Reaction equation
[CH3:1][NH:2][CH3:3].Cl.[CH2:5]([O:7][CH:8]([O:10][CH:11]([CH:20]1[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]1)[CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:9])[CH3:6].[C-:27]#[N:28].[K+]>O.O1CCCC1.CO>[CH3:1][N:2]([CH3:3])[C:23]1([C:27]#[N:28])[CH2:24][CH2:25][CH:20]([CH:11]([O:10][CH:8]([O:7][CH2:5][CH3:6])[CH3:9])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:21][CH2:22]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
40% aqueous dimethylamine solution (1.73 ml, 13.7 mmol) was added to a mixture of 4 M hydrochloric acid (747 μl) and methanol (448 μl), while cooling with ice, and the mixture was added to 4-[1-(1-ethoxy-ethoxy)-2-phenoxyethyl]cyclohexanone (880 mg, 2.87 mmol), before potassium cyanide (448 mg, 6.88 mg) was added. Tetrahydrofuran (3 ml) was also added for solubilization. The reaction mixture was stirred at room temperature for 6 h, water (50 ml) was then added and the mixture was extracted with diethyl ether (4×30 ml). The combined organic phases were concentrated in vacuo, the residue was taken up in methylene chloride (30 ml) and the mixture was washed with water (30 ml). The organic phase was dried with sodium sulfate and concentrated in vacuo.
Workup
- temperaturewhile cooling with ice
- additionwas added
- extractionthe mixture was extracted with diethyl ether (4×30 ml)
- concentrationThe combined organic phases were concentrated in vacuo
- washthe mixture was washed with water (30 ml)
- dry with materialThe organic phase was dried with sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-d86665b5a3eb4b22a0700b53a536f38f
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08288406B2
Reaction notes
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