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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
ノート
印刷プレビュー

反応式

HRID 273999 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7222deb64b3e445db32427f5aa03b346
出典データセット
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05387685

反応ノート

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