Phenyl(tricyclo[2.2.1.0~2,6~]heptan-3-yl)methanone → HCID 53839787, compound

HRID 462141Notes

Reaction equation

HRID 462141 reaction equation
[C:1]1([C:7]([CH:9]2[CH:14]3[CH2:15][CH:11]4[CH:12]([CH2:13]3)[CH:10]24)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][N:17]1[CH2:21][CH2:20][CH2:19][CH:18]1[CH:22](Cl)[CH3:23]>CS(C)=O>[CH3:16][N:17]1[CH2:21][CH2:20][CH2:19][CH:18]1[CH2:22][CH2:23][O:8][C:7](=[C:9]1[CH:14]2[CH2:15][CH:11]3[CH:12]([CH2:13]2)[CH:10]13)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 94017Phenyl(tricyclo[2.2.1.0~2,6~]heptan-3-yl)methanoneHCID 12244200HCID 12244200, compound

Product 1

HCID 53839787HCID 53839787, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

5.28 g. (0.11 mol) of a 50% sodium hydride/mineral oil dispersion were purified as in Example 6, followed by the dropwise addition while stirring under nitrogen of 80 ml. of dimethyl sulphoxide. The reaction mixture was then heated for 30 minutes at 70°-80° C. until the evolution of hydrogen stopped, after which it was cooled to room temperature and a solution of 19.83 g. (0.1 mol) of tricyclo-(2.2.1.02.6)-hept-3-yl phenyl ketone in 25 ml. of dimethyl sulphoxide added dropwise to it. After stirring for another hour at 35°-40° C., 16.25 g. (0.11 mol) of N-methyl pyrrolidyl-2-ethyl chloride in 15 ml. of dimethyl sulphoxide were added and the mixture stirred for another 2.5 hours at 35° to 40° C. The reaction mixture was then poured into 300 ml. of water, the oil precipitated was extracted with ether and the ether phase dried with anhydrous sodium sulphate. Filtration and concentration of the solvent by evaporation in vacuo left an oily residue which was converted into the hydrochloride in chloroform with 2N hydrochloric acid.

Workup

  1. custom(0.11 mol) of a 50% sodium hydride/mineral oil dispersion were purified as in Example 6
  2. additionfollowed by the dropwise addition
  3. temperatureThe reaction mixture was then heated for 30 minutes at 70°-80° C. until the evolution of hydrogen
  4. stirringAfter stirring for another hour at 35°-40° C.
  5. stirringthe mixture stirred for another 2.5 hours at 35° to 40° C
  6. additionThe reaction mixture was then poured into 300 ml
  7. customof water, the oil precipitated
  8. extractionwas extracted with ether
  9. dry with materialthe ether phase dried with anhydrous sodium sulphate
  10. filtrationFiltration and concentration of the solvent
  11. customby evaporation in vacuo
  12. waitleft an oily residue which

Sources & evidence

ORD record
ord-9e604f0455f8462fa1bc1a72b4281734
Source dataset
uspto-grants-1977_12
Patent number
US04065501

Reaction notes

Loading…