Phosgene → 5,10-Dihydro-5-{[(1-methyl-4-piperidinyl)oxy]carbonyl}-11H-dibenzo[b,e][1,4]diazepin-11-one

HRID 325884

反応式

HRID 325884 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1.[C:9](Cl)(Cl)=[O:10].C(=O)([O-])[O-].[Na+].[Na+].[CH:19]1[C:29]2[C:28](=[O:30])[NH:27][C:26]3[CH:31]=[CH:32][CH:33]=[CH:34][C:25]=3[NH:24][C:23]=2[CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1.O1CCOCC1>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]([N:24]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:29]=3[C:28](=[O:30])[NH:27][C:26]3[CH:31]=[CH:32][CH:33]=[CH:34][C:25]2=3)=[O:10])[CH2:4][CH2:3]1

参加物

7

反応物 4

HCID 6371PhosgeneHCID 10340Sodium CarbonateHCID 660484-Piperidinol, 1-methyl-HCID 2013275,10-Dihydro-11H-dibenzo(b,e)(1,4)diazepin-11-one

生成物 1

HCID 132767485,10-Dihydro-5-{[(1-methyl-4-piperidinyl)oxy]carbonyl}-11H-dibenzo[b,e][1,4]diazepin-11-one

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 312751,4-Dioxane溶媒

実験手順

A quantity of 4.9 gm (0.0425 mol) of 1-methyl-4-piperidinol was added dropwise to a mixture of 22.5 ml of a 20% solution of phosgene in toluene, 100 ml of dioxane, and 4.75 gm (0.045 mol) of anhydrous sodium carbonate while external cooling with ice was carried out. The mixture was stirred for a further 60 minutes at ambient temperature, 9.0 gm (0.0428 mol) of 5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one were added to the reaction mixture, and this was then refluxed for four hours. The mixture was filtered, the filtrate was concentrated by evaporation in vacuo, and the crude product obtained was purified by column chromatography on 500 gm of silica gel [eluant: ethyl acetate/methanol (volume ratio of 10:1)]. After recrystallization from ethyl acetate, the resulting colorless crystals melted at 203°-204° C. and were identical--according to the mixed melting point, thin layer chromatogram, and IR spectrum--to a product prepared according to Example 4. Yield: 7.6 gm (51% of theory).

後処理

  1. temperaturewhile external cooling with ice
  2. temperaturethis was then refluxed for four hours
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated by evaporation in vacuo

出典と根拠

ORDレコード
ord-0175f5fc7cb344e9ae00fa40432413e2
出典データセット
uspto-grants-1984_04
特許番号
US04443452

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