Sulphobenzoic anhydride → 4-(2-Acetyl-9-thioxanthenylidene)-1-methyl-piperidine

HRID 1680688Notes

Reaction equation

HRID 1680688 reaction equation
[C:1]([C:4]1[CH:17]=[CH:16][C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]([CH:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)(O)[C:6]=2[CH:5]=1)(=[O:3])[CH3:2].S(C1C=CC=CC=1C(OC(=O)C1C=CC=CC=1S(O)(=O)=O)=O)(O)(=O)=O>C(O)(=O)CC>[C:1]([C:4]1[CH:17]=[CH:16][C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[C:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)[C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 13795534Sulphobenzoic anhydrideHCID 205559562-Acetyl-9-(1-methyl-4-piperidyl)-9-thioxanthenol

Product 1

HCID 205559284-(2-Acetyl-9-thioxanthenylidene)-1-methyl-piperidine

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Procedure

140 grams of the ethylene glycal ketal of 2-acetyl-9-(1-methyl-4-piperidyl)-9-thioxanthenol (MP 206-208 degrees Centigrade) were heated for two hours under reflux with a mixture of 1500 milliliters of propionic acid and 100 grams of 2-sulfobenzoic acid anhydride. Thereafter the mixture was evaporated in vacuum, the residue dissolved in water and made alkaline. The base which separated out was extracted with ether, the ether phase dried over anhydrous potassium carbonate and evaporated until beginning crystallization. The crystals were sucked off and dried. - 50 grams of 4-(2-acetyl-9-thioxanthenylidene)-1-methyl-piperidine were obtained melting at 125-127 degrees Centigrade.

Workup

  1. customThereafter the mixture was evaporated in vacuum
  2. dissolutionthe residue dissolved in water
  3. customThe base which separated out
  4. extractionwas extracted with ether
  5. dry with materialthe ether phase dried over anhydrous potassium carbonate
  6. customevaporated
  7. customcrystallization
  8. customdried

Sources & evidence

ORD record
ord-b3bbf1c5f9744470915548d462cd34c8
Source dataset
uspto-grants-1981_06
Patent number
US04275209

Reaction notes

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