Sodium Hydroxide → 4-[6-[[6-Methoxy-4-methyl-8-quinolinyl]amino]hexyl]-1-piperazinepropanol

HRID 542836ノート

反応式

HRID 542836 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([NH:28][C:29]2[CH:30]=[C:31]([O:40][CH3:41])[CH:32]=[C:33]3[C:38]=2[N:37]=[CH:36][CH:35]=[C:34]3[CH3:39])=O)[CH2:17][CH2:16]1.[OH-].[Na+]>O1CCCC1.O>[CH3:41][O:40][C:31]1[CH:32]=[C:33]2[C:38](=[C:29]([NH:28][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][N:18]3[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][CH2:12][OH:11])[CH2:16][CH2:17]3)[CH:30]=1)[N:37]=[CH:36][CH:35]=[C:34]2[CH3:39]

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 202071744-(3-hydroxypropyl)-N-(6-methoxy-4-methyl-8-quinolinyl)-1-piperazinehexanamideHCID 21226445Aluminium lithium hydride

生成物 1

HCID 5355704-[6-[[6-Methoxy-4-methyl-8-quinolinyl]amino]hexyl]-1-piperazinepropanol収率 49.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A cold (-40°) slurry of 1.8 g (0.0135 mole) of anhydrous aluminum chloride in 60 ml of tetrahydrofuran was added to an equally cold suspension of 1.5 g (0.039 mole) of lithium aluminum hydride in 30 ml of tetrahydrofuran. The mixture was stirred and allowed to warm to -10°. To it was added dropwise a solution of 4.4 g (0.0103 mole) of 4-(3-hydroxypropyl)-N-(6-methoxy-4-methyl-8-quinolinyl)-1-piperazinehexanamide in 15 ml of tetrahydrofuran. The mixture was stirred for 2 hr, then treated with 7 ml of 30% sodium hydroxide solution and enough water to clarify the supernatant and finally filtered through supercell. The filtrate was concentrated in vacuo to remove tetrahydrofuran, diluted with dichloromethane, washed with water, dried, and concentrated to dryness. The residue was chromatographed over 200 g of silica gel with a 15:84:1 mixture of methanol:ethyl acetate-triethylamine. That portion of the eluant containing the product, Rf(silica--25:74:1 mixture of methanol:ethyl acetate:triethylamine)=0.33, was concentrated to dryness in vacuo. Recrystallization of the residue from 2-propanol afforded 2.1 g (49%) of the title compound, mp 100°-102°.

後処理

  1. temperatureto warm to -10°
  2. stirringThe mixture was stirred for 2 hr
  3. filtrationfinally filtered through supercell
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto remove tetrahydrofuran
  6. additiondiluted with dichloromethane
  7. washwashed with water
  8. customdried
  9. concentrationconcentrated to dryness
  10. customThe residue was chromatographed over 200 g of silica gel with a 15:84:1 mixture of methanol
  11. additionThat portion of the eluant containing
  12. additionthe product, Rf(silica--25:74:1 mixture of methanol:ethyl acetate:triethylamine)=0.33
  13. concentrationwas concentrated to dryness in vacuo
  14. customRecrystallization of the residue from 2-propanol

出典と根拠

ORDレコード
ord-7bb0b933c88c49f69802ee9225e87411
出典データセット
uspto-grants-1987_04
特許番号
US04659708

反応ノート

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