Maleic Acid → HCID 66861273, compound

HRID 869087Notes

Reaction equation

HRID 869087 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]\[C:25]([OH:27])=[O:26]>C(OCC)(=O)C>[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]\[C:25]([OH:27])=[O:26].[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]1[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 9966051Vortioxetine

Product 1

HCID 66861273HCID 66861273, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

2.5 gram 1-[2-(2,4-Dimethylphenylsulfanyl)-phenyl]piperazine oil was dissolved in 50 ml ethyl acetate and heated to 60° C. followed by addition of 1.1 gram maleic acid. The mixture was heated again to reflux for 5 minutes and left to cool to room temperature while stirring. During the cooling precipitation started and was finalized by 4 hours in the freezer (−18° C.). The white solid was collected by filtration and washed with 50 ml diethyl ether before drying in vacuum (50° C.) over night. This produced 1.3 gram of 1-[2-(2,4-Dimethylphenylsulfanyl)-phenyl]piperazine Maleate (38%) that was recrystallised by treatment with 40 ml ethyl acetate and 5 ml methanol at reflux. The clear solution was cooled to room temperature followed by 2 hours in the freezer (−18° C.) before filtering and washed twice with 10 ml cold ethyl acetate followed by drying in vacuum (50° C.) for two days. 1-[2-(2,4-Dimethylphenylsulfanyl)-phenyl]piperazine Maleate was isolated in 0.9 gram (69%).

Workup

  1. temperatureThe mixture was heated again
  2. temperatureto reflux for 5 minutes
  3. waitleft
  4. temperatureto cool to room temperature
  5. customDuring the cooling precipitation
  6. filtrationThe white solid was collected by filtration
  7. washwashed with 50 ml diethyl ether
  8. custombefore drying in vacuum (50° C.) over night
  9. customThis produced 1.3 gram of 1-[2-(2,4-Dimethylphenylsulfanyl)-phenyl]piperazine Maleate (38%) that was recrystallised by treatment with 40 ml ethyl acetate and 5 ml methanol
  10. temperatureat reflux
  11. temperatureThe clear solution was cooled to room temperature
  12. waitfollowed by 2 hours in the freezer (−18° C.)
  13. filtrationbefore filtering
  14. washwashed twice with 10 ml cold ethyl acetate
  15. customby drying in vacuum (50° C.) for two days

Sources & evidence

ORD record
ord-e3ef4e872b5b4327b58293abbf65eae8
Source dataset
uspto-grants-2015_03
Patent number
US08969355B2

Reaction notes

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