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Sodium Iodide → 2-[6-(3,4-Dimethoxyphenyl)-6-[(4-methylphenyl)thio]-hexyl]-1,2,3,4-tetrahydro-6-methoxyisoquinoline

HRID 273999
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반응식

HRID 273999 반응식
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)[S:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1.[CH3:26][O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[CH2:34][NH:33][CH2:32][CH2:31]2.C(N(C(C)C)CC)(C)C.[I-].[Na+]>C(#N)C>[CH3:25][O:24][C:18]1[CH:17]=[C:16]([CH:7]([S:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:33]2[CH2:32][CH2:31][C:30]3[C:35](=[CH:36][CH:37]=[C:28]([O:27][CH3:26])[CH:29]=3)[CH2:34]2)[CH:21]=[CH:20][C:19]=1[O:22][CH3:23]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinolineHCID 81531DiisopropylethylamineHCID 108122034-[6-Bromo-1-[(4-methylphenyl)thio]hexyl]-1,2-dimethoxybenzene

생성물 1

HCID 106731562-[6-(3,4-Dimethoxyphenyl)-6-[(4-methylphenyl)thio]-hexyl]-1,2,3,4-tetrahydro-6-methoxyisoquinoline

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

To a solution of 4.23 g of 4-[6-bromo-1-[(4-methylphenyl)thio]hexyl]-1,2-dimethoxybenzene in 40 mL of acetonitrile is added 3.88 g of 6-methoxy-1,2,3,4-tetrahydroisoquinoline, 1.74 mL of diisopropylethylamine and 0.01 g of sodium iodide. The solution is heated to reflux for 43 hours and cooled to room temperature. The reaction mixture is partitioned between chloroform and aqueous potassium carbonate and the organic layer is dried over magnesium sulfate. The volatiles are removed at reduced pressure and the residue chromatographed on silica gel using a gradient elution of hexane to chloroform to methyl alcohol. The residue from the chromatography is dissolved in diethyl ether and passed through diatomaceous earth. This affords 4.4 g of the desired product as a yellow oil.

후처리

  1. temperatureThe solution is heated
  2. temperatureto reflux for 43 hours
  3. customThe reaction mixture is partitioned between chloroform and aqueous potassium carbonate
  4. dry with materialthe organic layer is dried over magnesium sulfate
  5. customThe volatiles are removed at reduced pressure
  6. customthe residue chromatographed on silica gel using
  7. washa gradient elution of hexane to chloroform to methyl alcohol
  8. dissolutionThe residue from the chromatography is dissolved in diethyl ether

출처 및 근거

ORD 기록
ord-7222deb64b3e445db32427f5aa03b346
출처 데이터셋
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05387685

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