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

HRID 863880노트

반응식

HRID 863880 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-209c5ba6fd664232b82b79801fde39ed
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05561141

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