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

HRID 1105636Notes

Reaction equation

HRID 1105636 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-0da4820d020b46b094d3bcc1ce6b9519
Source dataset
uspto-grants-1982_01
Patent number
US04309429

Reaction notes

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