Water → HCID 21480569, compound

HRID 1490163Notes

Reaction equation

HRID 1490163 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6](CC2CCC(=O)CC2)=[CH:5][CH:4]=1.[NH:17]1CC[CH2:19][CH2:18]1.[OH2:22].[C:23]1([CH3:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:18]([CH2:19][CH2:29][CH:23]1[CH2:28][CH:27]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:16][CH:15]=2)[CH2:26][CH2:25][C:24]1=[O:22])#[N:17]

Participants

6

Reactant 4

HCID 962Water2×HCID 1140TolueneHCID 31268PyrrolidineHCID 2817579HCID 2817579, compound

Product 1

HCID 21480569HCID 21480569, compound

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

4-(4-Methoxybenzyl)cyclohexanone (112 g) (prepared as described in Example 1 (a)) pyrrolidine (100 g), and p-toluene sulphonic acid (0.3 g) were dissolved in toluene (1.56) and heated to reflux under argon with Dean-Stark water separation. When water ceased to separate (ca 2.5 hours) the remaining pyrrolidine and solvent were evaporated off and the residue dissolved in absolute ethanol (1 litre). The product was treated with acrylonitrile (27.2 g) in ethanol (30 ml). After 2 hours at reflux the reaction was left to cool and then concentrated in vacuo. The residue was treated with water (1 litre) and acetic acid (200 ml). After stirring for 2 hours the mixture was extracted into diethyl ether and the organic phase dried (Na2SO4) and concentrated to yield 2-(2-cyanoethyl)-4-(4-methoxyphenyl)cyclohexanone as an oil (140 g).

Workup

  1. temperatureheated
  2. customto separate (ca 2.5 hours) the remaining pyrrolidine and solvent
  3. customwere evaporated off
  4. dissolutionthe residue dissolved in absolute ethanol (1 litre)
  5. additionThe product was treated with acrylonitrile (27.2 g) in ethanol (30 ml)
  6. temperatureAfter 2 hours at reflux the reaction
  7. waitwas left
  8. temperatureto cool
  9. concentrationconcentrated in vacuo
  10. additionThe residue was treated with water (1 litre) and acetic acid (200 ml)
  11. extractionwas extracted into diethyl ether
  12. dry with materialthe organic phase dried (Na2SO4)
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-5c46d58b4e954f518a8eab4c3144cf1c
Source dataset
uspto-grants-1997_10
Patent number
US05681839

Reaction notes

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