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

HRID 1973842
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HRID 1973842 반응식
[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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 7909Methyl Isobutyl Ketone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-580640e617b6415e9dca8031a4fe9fca
출처 데이터셋
uspto-grants-1976_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US03998834

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