Sodium Carbonate → N-{1-[2-(2-furanyl)ethyl]-4-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide ethanedioate

HRID 1448340Notes

Reaction equation

HRID 1448340 reaction equation
[C:1](=[O:4])([O-:3])[O-].[Na+].[Na+].[CH3:7][O:8][CH2:9][C:10]1([N:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17](=[O:20])[CH2:18][CH3:19])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.CC1C=CC(S(O[CH2:38][CH2:39][C:40]2[O:41][CH:42]=[CH:43][CH:44]=2)(=O)=[O:35])=CC=1>CC(C)CC(=O)C>[C:17]([OH:20])(=[O:35])[C:1]([OH:3])=[O:4].[O:41]1[CH:42]=[CH:43][CH:44]=[C:40]1[CH2:39][CH2:38][N:13]1[CH2:14][CH2:15][C:10]([N:16]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:17](=[O:20])[CH2:18][CH3:19])([CH2:9][O:8][CH3:7])[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 162172NoralfentanilHCID 103331462-(Furan-2-yl)ethyl 4-methylbenzene-1-sulfonate

Product 1

HCID 86734317N-{1-[2-(2-furanyl)ethyl]-4-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide ethanedioateYield 39.1%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a stirred and refluxing mixture of 9.5 parts of sodium carbonate and 240 parts of 4-methyl-2-pentanone are added 8.3 parts of N-[4-(methoxymethyl)-4-piperidinyl]-N-phenylpropanamide and 9.6 parts of [2-(2-furanyl)ethyl] 4-methylbenzenesulfonate (water-separator). The whole is stirred and refluxed for 21 hours. The reaction mixture is cooled to room temperature and poured onto water. The organic phase is separated, washed with water, dried, filtered and evaporated. The oily residue is purified 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 residue is converted into the ethanedioate salt in 2-propanol. The salt is filtered off and crystallized from 2-propanol, yielding 5.4 parts (39.1%) of N-{1-[2-(2-furanyl)ethyl]-4-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide ethanedioate; mp. 178.6° C.

Workup

  1. temperaturerefluxing
  2. stirringThe whole is stirred
  3. temperaturerefluxed for 21 hours
  4. additionpoured onto water
  5. customThe organic phase is separated
  6. washwashed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe oily residue is purified by column-chromatography over silica gel using
  11. additiona mixture of trichloromethane and 7% of methanol as eluent
  12. customThe pure fractions are collected
  13. customthe eluent is evaporated
  14. filtrationThe salt is filtered off
  15. customcrystallized from 2-propanol

Sources & evidence

ORD record
ord-6eb8a015c2184c128656232c987b7fb3
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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