Diethyl Ether → HCID 178521566, compound

HRID 895033Notes

Reaction equation

HRID 895033 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

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-4c00da12214b402392453f4fdfbf8e24
Source dataset
uspto-grants-1981_08
Patent number
US04285956

Reaction notes

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