Potassium Iodide → alpha-(3,4-Dimethoxyphenyl)-7-[2-(dimethylamino)ethoxy]-3, 4-dihydro-6-methoxy-alpha-[(4-methylphenyl)thio]-2(1H)-isoquinolineheptanenitrile

HRID 863880ノート

反応式

HRID 863880 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([S:32][C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][C:23]([OH:31])=[C:24]([O:29][CH3:30])[CH:25]=3)[CH2:20]2)[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].[CH3:42][N:43]([CH3:47])[CH2:44][CH2:45]Cl.[I-].[K+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([S:32][C:33]2[CH:34]=[CH:35][C:36]([CH3:39])=[CH:37][CH:38]=2)([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][C:23]([O:31][CH2:45][CH2:44][N:43]([CH3:47])[CH3:42])=[C:24]([O:29][CH3:30])[CH:25]=3)[CH2:20]2)[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 10721301alpha-(3,4-Dimethoxvphenyl)-3.4-dihydro-7-hydroxy-6-methoxy-alpha-[(4-methylphenyl)thio]-2(1H)-isoquinolineheptanenitrile

生成物 1

HCID 10770129alpha-(3,4-Dimethoxyphenyl)-7-[2-(dimethylamino)ethoxy]-3, 4-dihydro-6-methoxy-alpha-[(4-methylphenyl)thio]-2(1H)-isoquinolineheptanenitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 0.583 g of α-(3,4-dimethoxyphenyl)-3,4-dihydro-7-hydroxy-6-methoxy-α-[(4-methylphenyl)thio]-2(1H)-isoquinolineheptanenitrile in 20 mL of N,N-dimethylformamide is added 0.051 g of 60% sodium hydride in oil and the solution stirred for 1 hour. To this solution is added 0.34 g of freshly prepared 2-dimethylaminoethylchloride and 0.60 g of potassium iodide. The solution is stirred at room temperature for 18 hours and then the volatiles are removed at reduced pressure. The residue is dissolved in a minimum amount of ethyl acetate and 5 volumes of diethyl ether is added. This solution is passed through a short pad of hydrous magnesium silicate and the volatiles are removed at reduced pressure. The residue is chromatographed on silica gel using a gradient of diethyl ether to ethyl acetate to methyl alcohol. This afford 0.14 g of the desired product as a clear glass. MS(Hi res): m/z Calcd for C36H47N3O4S 617.3287 Found 617.3302

後処理

  1. stirringThe solution is stirred at room temperature for 18 hours
  2. customthe volatiles are removed at reduced pressure
  3. dissolutionThe residue is dissolved in a minimum amount of ethyl acetate and 5 volumes of diethyl ether
  4. additionis added
  5. customthe volatiles are removed at reduced pressure
  6. customThe residue is chromatographed on silica gel using a gradient of diethyl ether to ethyl acetate to methyl alcohol

出典と根拠

ORDレコード
ord-209c5ba6fd664232b82b79801fde39ed
出典データセット
uspto-grants-1996_10
特許番号
US05561141

反応ノート

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