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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
ノート
印刷プレビュー

反応式

HRID 1863036 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回
HCID 7909Methyl Isobutyl Ketone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8ee3f447175e46de814d7d339fb537dc
出典データセット
uspto-grants-1979_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04167574

反応ノート

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