Acrylonitrile → HCID 67407225, compound

HRID 2066957Notes

Reaction equation

HRID 2066957 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.[CH:17]1([NH2:23])CCC[CH2:19][CH2:18]1.C(#N)C=C>C1(C)C=CC=CC=1.C(O)(=O)C.COC1C=CC(O)=CC=1>[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:8][CH:7]([CH2:19][CH2:18][C:17]#[N:23])[C:6](=[O:9])[CH2:5][CH2:4]1

Participants

7

Reactant 3

HCID 7855AcrylonitrileHCID 7965CyclohexylamineHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 67407225HCID 67407225, compoundYield 813.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 90154-MethoxyphenolCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

4-(dimethylamino)-4-phenylcyclohexanone (2.17 g, 10 mmol) was added to a solution of cyclohexylamine (109 mg, 1 mmol), glacial acetic acid (26 mg, 0.43 mmol) and 4-methoxyphenol (26 mg, 0.21 mmol) in 10 ml of toluol. The mixture was heated to 90° C. (bath temperature) and mixed with acrylonitrile (4 ml, 60.8 mmol) within 2 h. The batch was then heated to 120° C. After 3 h the heating was removed and the batch mixed with 1N NaOH (20 ml) after RT was reached. The mixture obtained was extracted with ethyl acetate (3×20 ml). The combined organic phases were washed with water and then dried over MgSO4. The residue (2.2 g) obtained after removal of the solvent solidified upon standing and was mainly composed of the initial ketone and a more non-polar product compared to this. One of the two possible diastereoisomers of the ketone was obtained with a yield of 400 mg (14%) in the form of an oil by means of chromatographic purification [silica gel 60 G (10 g); cyclohexane/ethyl acetate 1:10 (120 ml)].

Workup

  1. temperatureThe batch was then heated to 120° C
  2. customAfter 3 h the heating was removed
  3. additionthe batch mixed with 1N NaOH (20 ml) after RT
  4. customThe mixture obtained
  5. extractionwas extracted with ethyl acetate (3×20 ml)
  6. washThe combined organic phases were washed with water
  7. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-9728c9d6bdf14b6b9b2bb9420f8b962d
Source dataset
uspto-grants-2012_10
Patent number
US08293758B2

Reaction notes

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