Sulfuric Acid → HCID 12298135, compound

HRID 1448310Notes

Reaction equation

HRID 1448310 reaction equation
S(=O)(=O)(O)O.[C:6]1([CH2:12][N:13]2[CH2:18][CH2:17][C:16]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)([C:19]#[N:20])[CH2:15][CH2:14]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-:32].[NH4+]>>[C:6]1([CH2:12][N:13]2[CH2:18][CH2:17][C:16]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:29])[F:30])[CH:23]=3)([C:19]([NH2:20])=[O:32])[CH2:15][CH2:14]2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 12298118HCID 12298118, compound

Product 1

HCID 12298135HCID 12298135, compound

Procedure

To 1656 parts of concentrated sulfuric acid are added portionwise 249.5 parts of 1-(phenylmethyl)-4-{[3-(trifluoromethyl)phenyl]amino}-4-piperidinecarbonitrile. Upon completion, stirring is continued overnight at room temperature. The reaction mixture is poured onto crushed ice and while cooling, the whole is alkalized with ammonium hydroxide. Upon stirring vigorously, the product precipitates. The supernatant aqueous phase is decanted and the residual solid product is dissolved in trichloromethane. The solution is shaken with ammonium hydroxide. The organic phase is washed with water, dried, filtered and evaporated. The solid residue is stirred in 2,2'-oxybispropane. The product is filtered off, washed with hexane and dried in vacuo, yielding 1-(phenylmethyl)-4-{[3-(trifluoromethyl)phenyl]amino}-4-piperidinecarboxamide; mp. 179.3° C.

Workup

  1. additionThe reaction mixture is poured
  2. customonto crushed ice
  3. temperaturewhile cooling
  4. stirringUpon stirring vigorously
  5. customthe product precipitates
  6. customThe supernatant aqueous phase is decanted
  7. dissolutionthe residual solid product is dissolved in trichloromethane
  8. stirringThe solution is shaken with ammonium hydroxide
  9. washThe organic phase is washed with water
  10. customdried
  11. filtrationfiltered
  12. customevaporated
  13. stirringThe solid residue is stirred in 2,2'-oxybispropane
  14. filtrationThe product is filtered off
  15. washwashed with hexane
  16. customdried in vacuo

Sources & evidence

ORD record
ord-d200b4c59b1543c18ce182f452aeab34
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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