Ammonium Chloride → 1-(6-Hydroxyhexyl)-5-chloro-3-methyl-2-(3-pyridyl)indole hydrochloride hemihydrate

HRID 1633130ノート

反応式

HRID 1633130 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:24]2[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=2)[C:18]([CH3:26])=[C:17]1[C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)=O.[Cl-:33].[NH4+]>O1CCCC1>[OH2:8].[ClH:25].[OH:8][CH2:9][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:24]2[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=2)[C:18]([CH3:26])=[C:17]1[C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1.[OH:8][CH2:9][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:24]2[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=2)[C:18]([CH3:26])=[C:17]1[C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1.[ClH:33]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 133621091-(5-Methoxycarbonylpentyl)-5-chloro-3-methyl-2-(3-pyridyl)indoleHCID 21226445Aluminium lithium hydride

生成物 1

HCID 705061921-(6-Hydroxyhexyl)-5-chloro-3-methyl-2-(3-pyridyl)indole hydrochloride hemihydrate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of 0.49 g of lithium aluminum hydride in 50 ml of anhydrous tetrahydrofuran under nitrogen is added dropwise at room temperature a solution of 3.92 g of 1-(5-methoxycarbonylpentyl)-5-chloro-3-methyl-2-(3-pyridyl)indole in 30 ml of anhydrous tetrahydrofuran. After addition is complete the suspension is stirred for 1 hour at room temperature, and 50 ml of a saturated ammonium chloride solution is added. The reaction mixture is allowed to stand at room temperature overnight and the organic layer is separated. The aqueous layer is filtered to remove salts and extracted with ethyl acetate (2×50 ml). The combined organic layers are washed with saturated brine, dried over magnesium sulfate and concentrated in vacuo. The crude product is purified by trituration with hexane/ether and dissolved in ethanol. Ethanolic hydrochloric acid is added to acidity and the solution diluted with anhydrous ether to crystallize the product. 1-(6-Hydroxyhexyl)-5-chloro-3-methyl-2-(3-pyridyl)indole hydrochloride hemihydrate, m.p. 115°-118°, is obtained.

後処理

  1. additionAfter addition
  2. waitto stand at room temperature overnight
  3. customthe organic layer is separated
  4. filtrationThe aqueous layer is filtered
  5. customto remove salts
  6. extractionextracted with ethyl acetate (2×50 ml)
  7. washThe combined organic layers are washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe crude product is purified by trituration with hexane/ether
  11. dissolutiondissolved in ethanol
  12. additionEthanolic hydrochloric acid is added to acidity
  13. additionthe solution diluted with anhydrous ether
  14. customto crystallize the product

出典と根拠

ORDレコード
ord-3cd0ab5ac39f47da8d83ea5fa44d56b7
出典データセット
uspto-grants-1984_10
特許番号
US04478842

反応ノート

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