N,N'-Dicyclohexylurea → HCID 178521558, compound

HRID 895034Notes

Reaction equation

HRID 895034 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10]([F:17])[CH:11]=3)[C:6](=[C:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[C:5]=2[CH:4]=1.[OH:26][C@@H:27]1[CH2:32][CH2:31][C@H:30]([CH2:33][C:34](O)=O)[CH2:29][CH2:28]1.C1(N=C=NC2CCCCC2)CCCCC1.C(NC1CCCCC1)(NC1CCCCC1)=O>C(Cl)Cl>[OH:26][C@@H:27]1[CH2:32][CH2:31][C@H:30]([CH2:33][CH2:34][N:21]2[CH2:20][CH2:19][C:18](=[C:6]3[C:5]4[CH:4]=[C:3]([C:2]([F:1])([F:24])[F:25])[CH:16]=[CH:15][C:14]=4[S:13][C:12]4[C:7]3=[CH:8][CH:9]=[C:10]([F:17])[CH:11]=4)[CH2:23][CH2:22]2)[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 4277N,N'-DicyclohexylureaHCID 10868DicyclohexylcarbodiimideHCID 20555920HCID 20555920, compoundHCID 178525568HCID 178525568, compound

Product 1

HCID 178521558HCID 178521558, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.3 Grams of 4-(2-trifluoromethyl-6-fluoro-9-thioxanthenylidene)-piperidine were dissolved in 50 milliliters of dry methylene chloride. Then 3.8 grams of cis-4-hydroxycyclohexane acetic acid (J.Am.Ch.Soc. 70, pg. 1898-99 (1948) and 5 grams of dicyclohexylcarbodiimide were added. The mixture was heated at temperatures from 22 to 30 degrees Centigrade during which the dicyclohexylurea formed separated out and was then left standing overnight. The precipitate was filtered from the solution which was then evaporated, and the residue was dissolved in ether. The solution was washed with dilute hydrochloric acid, dried over anhydrous potassium carbonate, filtered and evaporated. The residue, which was an oil, wad dried by evaporation in vacuum with toluene and consisted of somewhat impure 1-(cis-4-hydroxycyclohexylmethylcarbonyl)-4-(2-trifluoromethyl-6-fluoro-9-thioxanthenylidene)piperidine which was used without further purification in the next step. The oil was dissolved in dry ether, and 2 grams of lithium aluminium hydride were added in small portions. The mixture was heated under reflux for one hour. Then water was added dropwise until the precipitate formed clotted. The ether phase was decanted, the precipitate washed thoroughly with ether, the combined ether phases were dried over anhydrous potassium carbonate and treated with active carbon and filtered. The ether was evaporated, and 1-(cis-4-hydroxycyclohexylethyl)-4-(2-trifluoromethyl-6-fluoro-9-thioxanthenylidene)piperidine was obtained as a yellow oil.

Workup

  1. customformed
  2. customseparated out
  3. waitwas then left
  4. filtrationThe precipitate was filtered from the solution which
  5. customwas then evaporated
  6. dissolutionthe residue was dissolved in ether
  7. washThe solution was washed with dilute hydrochloric acid
  8. dry with materialdried over anhydrous potassium carbonate
  9. filtrationfiltered
  10. customevaporated
  11. dry with materialwad dried by evaporation in vacuum with toluene
  12. customwas used without further purification in the next step
  13. dissolutionThe oil was dissolved in dry ether
  14. addition2 grams of lithium aluminium hydride were added in small portions
  15. temperatureThe mixture was heated
  16. temperatureunder reflux for one hour
  17. additionThen water was added dropwise until the precipitate
  18. customformed
  19. customThe ether phase was decanted
  20. washthe precipitate washed thoroughly with ether
  21. dry with materialthe combined ether phases were dried over anhydrous potassium carbonate
  22. additiontreated with active carbon
  23. filtrationfiltered
  24. customThe ether was evaporated

Sources & evidence

ORD record
ord-d562ddc4312040fc9baa6f8689dfb43a
Source dataset
uspto-grants-1981_08
Patent number
US04285956

Reaction notes

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