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Sodium Cyanide → (+/-)-cis-6-[4-(N-methylaminocarbonyl)phenyl]-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridine

HRID 635824
ノート
印刷プレビュー

反応式

HRID 635824 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[C@H:13]1[C@H:8]([CH2:9][CH2:10][CH2:11][CH2:12]1)[N:7]=[C:6]2[C:19]1[CH:24]=[CH:23][C:22]([C:25]([O:27]C)=O)=[CH:21][CH:20]=1.[C-:29]#[N:30].[Na+]>CN.C(O)C>[CH3:29][NH:30][C:25]([C:22]1[CH:21]=[CH:20][C:19]([C:6]2[C:5]3[C:14](=[CH:15][C:16]([O:17][CH3:18])=[C:3]([O:2][CH3:1])[CH:4]=3)[C@H:13]3[C@H:8]([CH2:9][CH2:10][CH2:11][CH2:12]3)[N:7]=2)=[CH:24][CH:23]=1)=[O:27]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 8929Sodium CyanideHCID 70021069(+/-)-cis-8,9-Dimethoxy-6-[4-(methoxycarbonyl)phenyl]-1,2,3,4,4a,10b-hexahydrophenanthridine

生成物 1

HCID 131722392(+/-)-cis-6-[4-(N-methylaminocarbonyl)phenyl]-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridine

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6329Methylamine溶媒

実験手順

680 mg of (+/−)-cis-8,9-dimethoxy-6-[4-(methoxycarbonyl)phenyl]-1,2,3,4,4a,10b-hexahydrophenanthridine with 25 mg of sodium cyanide in 13 ml of 9 molar methylamine solution in ethanol are heated to 90° C. in an autoclave for 10 h. The solution is concentrated under reduced pressure and the residue is taken up in methylene chloride and extracted with water. The organic phase is dried with sodium sulfate, the solvent is removed under reduced pressure and the residue is treated with diethyl ether, filtered off with suction and dried. This gives 380 mg (56.1 % of Th.) of the title compound of m.p. 209-211° C.

後処理

  1. concentrationThe solution is concentrated under reduced pressure
  2. extractionextracted with water
  3. dry with materialThe organic phase is dried with sodium sulfate
  4. customthe solvent is removed under reduced pressure
  5. additionthe residue is treated with diethyl ether
  6. filtrationfiltered off with suction
  7. customdried

出典と根拠

ORDレコード
ord-928b18d75baa4785b881fc5033d8e72a
出典データセット
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06191138B1

反応ノート

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