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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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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1863036
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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Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 7909Methyl Isobutyl KetoneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8ee3f447175e46de814d7d339fb537dc
Quelldatensatz
uspto-grants-1979_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04167574

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