Diethyl Ether → HCID 178521566, compound

HRID 1105637Notes

Reaction equation

HRID 1105637 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[C:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C[C:29]([CH2:31][CH:32]([CH3:34])[CH3:33])=O.CC[O:37][CH2:38][CH3:39]>>[OH:37][C@@H:38]1[CH2:39][CH2:33][C@H:32]([CH2:34][N:19]2[CH2:20][CH2:21][C:16](=[C:5]3[C:4]4[CH:3]=[C:2]([Cl:1])[CH:15]=[CH:14][C:13]=4[S:12][C:11]4[C:6]3=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH2:17][CH2:18]2)[CH2:31][CH2:29]1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 7909Methyl Isobutyl KetoneHCID 11430Potassium CarbonateHCID 133194264-(2-Chloro-9H-thioxanthen-9-ylidene)piperidine

Product 1

HCID 178521566HCID 178521566, compound

Procedure

24 Grams of cis-4-hydroxycyclohexanemethanol were dissolved in a mixture of 70 milliliters of dry pyridine and 100 milliliters of chloroform. At a temperature of -20 degrees Centigrade were added 23 grams of mesyl chloride dropwise while stirring. The mixture was kept at -10 to -20 degrees Centigrade for 2 hours while stirring, whereupon the mixture was left standing over night at room temperature. The reaction mixture was then poured into ice-water, the chloroform layer was separated off and washed with dilute hydrochloric acid. The chloroform phase was then dried over anhydrous magnesium sulphate, filtered and evaporated. The residue was distilled in vacuum and 30 grams of cis-(1-mesyloxymethyl-4-hydroxy)cyclohexane were obtained as an oil boiling at 120-125 degrees Centigrade/1 mm Hg. A mixture of 6 grams of 4-(2-chloro-9-thioxanthenylidene)-piperidine, 4-grams of cis-(1-mesyloxymethyl-4-hydroxy)-cyclohexane, 1.5 grams of finely crushed potassium carbonate and 25 milliliters of methylisobutylketone was heated under reflux for 5 hours while stirring. After cooling were added 200 milliliters of ether, and the organic phase was extracted with 5% aqueous methane sulphonic acid. The aqueous phase was made alkaline with aqueous ammonia, and the base which precipitated was extracted with ether. The etherphase was dried over anhydrous potassium carbonate, treated with active carbon and evaporated. The residue was crystallized from cyclohexane. Yield: 1.5 grams of 1-(cis-4-hydroxycyclohexylmethyl)-4-(2-chloro-9-thioxanthenylidene)piperidine, which melted at 100-103 degrees Centigrade.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter cooling
  4. extractionthe organic phase was extracted with 5% aqueous methane sulphonic acid
  5. customthe base which precipitated
  6. extractionwas extracted with ether
  7. dry with materialThe etherphase was dried over anhydrous potassium carbonate
  8. additiontreated with active carbon
  9. customevaporated
  10. customThe residue was crystallized from cyclohexane

Sources & evidence

ORD record
ord-3499a5a0742c43bdb04f8c46f0ccd8c3
Source dataset
uspto-grants-1982_01
Patent number
US04309429

Reaction notes

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