Dimethyl Sulfoxide → HCID 70612735, compound

HRID 1447657Notes

Reaction equation

HRID 1447657 reaction equation
CS(C)=O.[H-].[Na+].[CH3:7][N:8]([CH3:21])[C@@H:9]1[CH2:15][CH2:14][C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=2[C@H:11]([OH:20])[CH2:10]1.[F:22][C:23]1[CH:28]=[CH:27][C:26](F)=[CH:25][CH:24]=1>Cl>[CH3:7][N:8]([CH3:21])[C@@H:9]1[CH2:15][CH2:14][C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=2[C@H:11]([O:20][C:26]2[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=2)[CH2:10]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 108921,4-DifluorobenzeneHCID 24758Sodium hydrideHCID 86736721HCID 86736721, compound

Product 1

HCID 70612735HCID 70612735, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.6 ml of dimethylsulfoxide and 60 mg of sodium hydride in the form of a 50% oil dispersion was heated at 60° C. for 25 minutes and was then cooled to 25° C. after which 205 mg of cis 7-dimethylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol were added thereto. After 15 minutes, 0.4 ml of p-difluorobenzene were added thereto and the mixture was heated at 90° C. for 63/4 hours and was then cooled to 20° C. The mixture was extracted with methylene chloride and the organic phase was washed with water, dried and evaporated to dryness to obtain 350 mg of raw product which was dissolved in 10 ml of N hydrochloric acid. The solution was washed with ether and made alkaline with sodium hydroxide solution. The mixture was extracted with methylene chloride and the organic phase was washed with water, dried and evaporated to dryness to obtain 270 mg of cis N,N-dimethyl-5-[4-fluorophenoxy]-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-amine in the form of an oil.

Workup

  1. additionwere added
  2. temperaturethe mixture was heated at 90° C. for 63/4 hours
  3. temperaturewas then cooled to 20° C
  4. extractionThe mixture was extracted with methylene chloride
  5. washthe organic phase was washed with water
  6. customdried
  7. customevaporated to dryness
  8. customto obtain 350 mg of raw product which
  9. washThe solution was washed with ether
  10. extractionThe mixture was extracted with methylene chloride
  11. washthe organic phase was washed with water
  12. customdried
  13. customevaporated to dryness

Sources & evidence

ORD record
ord-0d6207092a7e4c60b7c27357dd3c6388
Source dataset
uspto-grants-1979_12
Patent number
US04177292

Reaction notes

Loading…