Imidazole → 1,2,3,4-Tetrahydro-2-[7-[3-[2-(1H-imidazol-1-yl)-ethoxy]-4-methoxyphenyl]-7-[(4-methylphenyl)thio]-heptyl]-6,7-dimethoxyisoquinoline

HRID 274009

반응식

HRID 274009 반응식
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[I-].[Na+].Cl[CH2:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH:22]([S:43][C:44]2[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][CH:45]=2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:29]2[CH2:38][CH2:37][C:36]3[C:31](=[CH:32][C:33]([O:41][CH3:42])=[C:34]([O:39][CH3:40])[CH:35]=3)[CH2:30]2)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21].[Si]([O-])([O-])([O-])[O-].[Mg+2].[Mg+2]>CN(C)C=O.C(OCC)(=O)C>[N:1]1([CH2:11][CH2:12][O:13][C:14]2[CH:15]=[C:16]([CH:22]([S:43][C:44]3[CH:45]=[CH:46][C:47]([CH3:50])=[CH:48][CH:49]=3)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:38][CH2:37][C:36]4[C:31](=[CH:32][C:33]([O:41][CH3:42])=[C:34]([O:39][CH3:40])[CH:35]=4)[CH2:30]3)[CH:17]=[CH:18][C:19]=2[O:20][CH3:21])[CH:5]=[CH:4][N:3]=[CH:2]1

참가 물질

8

반응물 5

HCID 795ImidazoleHCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 66225Magnesium orthosilicateHCID 107698442-[7-[3-(2-Chloroethoxy)-4-methoxyphenyl)-7-[(4-methylphenyl)thio]heptyl]-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline

생성물 1

HCID 108416971,2,3,4-Tetrahydro-2-[7-[3-[2-(1H-imidazol-1-yl)-ethoxy]-4-methoxyphenyl]-7-[(4-methylphenyl)thio]-heptyl]-6,7-dimethoxyisoquinoline수율 16,452%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매3회HCID 8857Ethyl Acetate용매

실험 절차

To 0.76 g of imidazole in 5 mL of 4A sieve-dried N,N-dimethylformamide is added 0.18 g of 60% sodium hydride in oil. When the effervescence subsides, 0.26 g of sodium iodide is added, followed by 1.12 g of 2-[7-[3-(2-chloroethoxy)-4-methoxyphenyl]-7[(4-methylphenyl)thio]heptyl]-1,2,3,4-tetrahydro-6,7dimethoxyisoquinoline in 5 mL of N,N-dimethylformamide. An additional 2 mL of N,N-dimethylformamide is used as wash. After letting the tan solution stand for 48 hours, it is concentrated in vacuo, and the residue is distributed between ethyl acetate and water. The organic layer is extracted with 1N hydrochloric acid, the acid layer basified with aqueous ammonia, and the resulting oil extracted into ethyl acetate. After drying (sodium sulfate), the extract is concentrated in vacuo to 0.53 g of tan oil. Flash chromatography of the oil on silica gel (gradient elution: hexane to chloroform to methyl alcohol) gives an oil which is taken up in ethyl acetate, passed through a pad of hydrous magnesium silicate, and concentrated to leave 0,194 g of the desired product as a yellow gum.

후처리

  1. washas wash
  2. customfor 48 hours
  3. concentrationit is concentrated in vacuo
  4. extractionThe organic layer is extracted with 1N hydrochloric acid
  5. extractionthe resulting oil extracted into ethyl acetate
  6. dry with materialAfter drying (sodium sulfate)
  7. concentrationthe extract is concentrated in vacuo to 0.53 g of tan oil
  8. customFlash chromatography of the oil on silica gel (gradient elution: hexane to chloroform to methyl alcohol) gives an oil which
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2524cec6c61640198916ce54ba40f2eb
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387685

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