Methyl iodide → HCID 12298199, compound

HRID 1448307Notes

Reaction equation

HRID 1448307 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2([C:23]([O-:25])=[O:24])[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[Na+].[CH3:27]N(C)P(=O)(N(C)C)N(C)C.IC>O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2([C:23]([O:25][CH3:27])=[O:24])[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:13][CH2:14]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 12679HexamethylphosphoramideHCID 70611387HCID 70611387, compound

Product 1

HCID 12298199HCID 12298199, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 19 parts of sodium 4-[N-(4-methylphenyl)amino]-1-(2-phenylethyl)-4-piperidinecarboxylate and 200 parts of hexamethylphosphoric triamide is heated to 80° C. for a while. After cooling, 12.3 parts of iodomethane are added dropwise at a temperature below 15° C. Upon completion, stirring is continued for 24 hours at room temperature. The reaction mixture is poured onto 600 parts of water and the product is extracted with trichloromethane. The extract is washed twice with water, dried, filtered and evaporated. The oily residue is poured onto 200 parts of water while stirring. The supernatant aqueous phase is decanted and the residual oil is dissolved in trichloromethane. The solution is washed with water, dried, filtered and evaporated. The residue is purified twice by column-chromatography over silica gel using a mixture of trichloromethane and 7% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The oily residue is suspended in 2,2'-oxybispropane. The product is filtered off and dried, yielding methyl 4-(4 -methylphenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate; mp. 94.5° C.

Workup

  1. temperatureAfter cooling
  2. extractionthe product is extracted with trichloromethane
  3. washThe extract is washed twice with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. additionThe oily residue is poured onto 200 parts of water
  8. stirringwhile stirring
  9. customThe supernatant aqueous phase is decanted
  10. dissolutionthe residual oil is dissolved in trichloromethane
  11. washThe solution is washed with water
  12. customdried
  13. filtrationfiltered
  14. customevaporated
  15. customThe residue is purified twice by column-chromatography over silica gel using
  16. additiona mixture of trichloromethane and 7% of methanol as eluent
  17. customThe pure fractions are collected
  18. customthe eluent is evaporated
  19. filtrationThe product is filtered off
  20. customdried

Sources & evidence

ORD record
ord-011d85414d5441d295e0e61241e45836
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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