Sulfuric Acid → HCID 131730603, compound

HRID 2098312Notes

Reaction equation

HRID 2098312 reaction equation
[CH3:1][CH:2]1[S:13][CH2:12][C:4]2([CH:9]3[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]3)[CH2:5]2)[O:3]1.[S:14](=[O:18])(=[O:17])([OH:16])[OH:15]>C1(C)C=CC=CC=1>[CH3:1][CH:2]1[S:13][CH2:12][C:4]2([CH:9]3[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]3)[CH2:5]2)[O:3]1.[S:14]([O-:18])([O-:17])(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 2684Evoxac

Product 1

HCID 131730603HCID 131730603, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
2.5 °C

Procedure

Charged toluene (50 ml) and to this charged cevimeline free base with cis isomer >90% (5.0 g) (prepared by any one of the above methods given in examples III to V). Stirred for 10 to 15 minutes to obtain a clear solution. Cooled the solution to 0 to 5° C. Charged concentrated sulfuric acid (1.3 ml) drop wise over 30 minutes and stir the resultant liberated sulfate salt for 30 minutes at 0 to 5° C. Then slowly raised the temperature to reflux temperature (100 to 115° C.) and continued the reflux for 60 to 90 minutes. The reaction mass was then cooled and processed as in Example VI to yield 3.5 g of cevimeline sulfate with cis isomer >97% purity by HPLC.

Workup

  1. customto obtain a clear solution
  2. stirringstir the resultant
  3. customfor 30 minutes
  4. customat 0 to 5° C
  5. temperatureThen slowly raised the temperature
  6. temperatureto reflux temperature (100 to 115° C.)
  7. temperaturereflux for 60 to 90 minutes
  8. temperatureThe reaction mass was then cooled

Sources & evidence

ORD record
ord-9536e292e0f648cda83d39d9c64f42ed
Source dataset
uspto-grants-2013_05
Patent number
US08450487B2

Reaction notes

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