Methanesulfonic Acid → HCID 88800164, compound

HRID 2083761Notes

Reaction equation

HRID 2083761 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[O: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:22](OC(=O)C)(=O)[CH3:23].C(=O)([O-])[O-].[K+].[K+].[CH3:35][S:36]([OH:39])(=[O:38])=[O:37]>O.CC(C)=O>[CH3:35][S:36]([OH:39])(=[O:38])=[O:37].[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[C:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH3:23])[CH2:18][CH2:17]3)[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 20357485HCID 20357485, compound

Product 1

HCID 88800164HCID 88800164, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 4-(2-chloro-9-xanthenylidene)piperidine (2.0 g., 6.75 mmol) in 5 ml. of acetic anhydride is heated on a steam bath for 2.5 hours. Acetone (30 ml.) and 50 ml. and 20% aqueous potassium carbonate is added to the cooled solution and the mixture stirred for one hour. Additional water is added and the mixture is extracted with ether. The extract is washed with 1N hydrochloric acid, water and dried. The solvent is evaporated to give the crude amide, 2.2 g. (recrystallized amide m.p. 165°-166° C.). The amide is dissolved in 500 ml. of ether and added to a stirred suspension of 2.0 g. of lithium aluminum hydride in 200 ml. of ether. After two hours at 23° C. excess hydride is decomposed with water (4 ml.) and 10% sodium hydrixode (3.2 ml.). The mixture is filtered and the filtrate is evaporated. The residue is dissolved in a mixture of methanol and ether and treated with one equivalent of methanesulfonic acid. The precipitated salt is filtered and recrystallized from methanol/ether to give 4-(2-chloro-9-xanthenylidene)-1-ethylpiperidine methanesulfonate, m.p. 249°-252° C.

Workup

  1. extractionthe mixture is extracted with ether
  2. washThe extract is washed with 1N hydrochloric acid, water
  3. customdried
  4. customThe solvent is evaporated
  5. customto give the crude amide, 2.2 g
  6. custom(recrystallized amide m.p. 165°-166° C.)
  7. dissolutionThe amide is dissolved in 500 ml
  8. additionof ether and added to a stirred suspension of 2.0 g
  9. waitAfter two hours at 23° C. excess hydride is decomposed with water (4 ml.) and 10% sodium hydrixode (3.2 ml.)
  10. filtrationThe mixture is filtered
  11. customthe filtrate is evaporated
  12. dissolutionThe residue is dissolved in a mixture of methanol and ether
  13. filtrationThe precipitated salt is filtered
  14. customrecrystallized from methanol/ether

Sources & evidence

ORD record
ord-0215c73496594d77a834301209c6adb0
Source dataset
uspto-grants-1978_04
Patent number
US04086350

Reaction notes

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