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Potassium Iodide → N-{1-[2-(4,5-dihydro-4-methyl-5-oxo-1H-tetrazol-1-yl)ethyl]-4-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide ethanedioate

HRID 1863036
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HRID 1863036 반응식
I[CH2:2][CH2:3][N:4]1[C:8](=[O:9])[N:7]([CH3:10])[N:6]=[N:5]1.[CH3:11][O:12][CH2:13][C:14]1([N:20]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21](=[O:24])[CH2:22][CH3:23])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[C:31](=O)([O-:33])[O-:32].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[C:8]([OH:9])(=[O:12])[C:31]([OH:33])=[O:32].[CH3:10][N:7]1[C:8](=[O:9])[N:4]([CH2:3][CH2:2][N:17]2[CH2:18][CH2:19][C:14]([N:20]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:21](=[O:24])[CH2:22][CH3:23])([CH2:13][O:12][CH3:11])[CH2:15][CH2:16]2)[N:5]=[N:6]1
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참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 162172NoralfentanilHCID 136767191,4-dihydro-1-(2-iodoethyl)-4-methyl-5H-tetrazol-5-one

생성물 1

HCID 13676754N-{1-[2-(4,5-dihydro-4-methyl-5-oxo-1H-tetrazol-1-yl)ethyl]-4-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide ethanedioate수율 42%

시약·촉매·용매 2

HCID 962Water용매2회
HCID 7909Methyl Isobutyl Ketone용매

실험 절차

A mixture of 2.55 parts of 1,4-dihydro-1-(2-iodoethyl)-4-methyl-5H-tetrazol-5-one, 3.45 parts of N-[4-(methoxymethyl)-4-piperidinyl]-N-phenylpropanamide, 2 parts of sodium carbonate, 0.2 parts of potassium iodide and 160 parts of 4-methyl-2-pentanone is stirred and refluxed overnight with water-separator. The reaction mixture is cooled, 100 parts of water are added and the layers are separated. The aqueous phase is extracted with dichloromethane. The combined organic phases are dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is converted into the ethanedioate salt in 2-propanone. The salt is filtered off and crystallized from 2-propanone, yielding 2.1 parts (42%) of N-{1-[2-(4,5-dihydro-4-methyl-5-oxo-1H-tetrazol-1-yl)ethyl]-4-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide ethanedioate (1:1); mp. 155.9° C.

후처리

  1. temperatureThe reaction mixture is cooled
  2. customthe layers are separated
  3. extractionThe aqueous phase is extracted with dichloromethane
  4. customThe combined organic phases are dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. filtrationThe salt is filtered off
  12. customcrystallized from 2-propanone

출처 및 근거

ORD 기록
ord-8ee3f447175e46de814d7d339fb537dc
출처 데이터셋
uspto-grants-1979_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04167574

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