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Toluene-4-sulfonic acid 1-methyl-piperidin-3-ylmethyl ester → (4-Isopropyl-piperazin-1-yl)-[1-(1-methyl-piperidin-3-ylmethyl)-1H-indol-5-yl]-methanone

HRID 2113470
ノート
印刷プレビュー

反応式

HRID 2113470 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([N:12]3[CH2:17][CH2:16][N:15]([CH:18]([CH3:20])[CH3:19])[CH2:14][CH2:13]3)=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CC([O-])(C)C.[K+].[CH3:27][N:28]1[CH2:33][CH2:32][CH2:31][CH:30]([CH2:34]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:29]1>C1COCC1>[CH:18]([N:15]1[CH2:14][CH2:13][N:12]([C:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[N:1]([CH2:34][CH:30]2[CH2:31][CH2:32][CH2:33][N:28]([CH3:27])[CH2:29]2)[CH:2]=[CH:3]3)=[O:11])[CH2:17][CH2:16]1)([CH3:20])[CH3:19]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 21184160Toluene-4-sulfonic acid 1-methyl-piperidin-3-ylmethyl ester2 回HCID 23665647Potassium tert-butoxideHCID 57752818Methanone,1h-indol-5-yl[4-(1-methylethyl)-1-piperazinyl]-2 回

生成物 1

HCID 23652334(4-Isopropyl-piperazin-1-yl)-[1-(1-methyl-piperidin-3-ylmethyl)-1H-indol-5-yl]-methanone収率 96.5%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

A mixture of 1.06 g (3.9 mmol) (1H-indol-5-yl)-(4-isopropyl-piperazin-1-yl)-methanone (intermediate 1); 0.484 g (4.3 mmol) KOtBu and 1.33 g (4.7 mmol) toluene-4-sulfonic acid 1-methyl-piperidin-3-ylmethyl ester (intermediate 6) in 20 mL THF was shaken at 60° C. for 3 h. After evaporation of all volatiles a mixture ethyl acetate was added and washed with water. The organic phase was dried with MgSO4 and evaporated to dryness. The residue was purified by column chromatography on silica eluting with a solvent mixture formed from DCM, methanol NEt3. The combined product fractions were evaporated to yield 1.44 g (91%) of the title compound as light yellow gum. MS(m/e): 383.5 (MH+).

後処理

  1. customAfter evaporation of all volatiles a mixture ethyl acetate
  2. additionwas added
  3. washwashed with water
  4. dry with materialThe organic phase was dried with MgSO4
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography on silica eluting with a solvent mixture
  7. customformed from DCM, methanol NEt3
  8. customThe combined product fractions were evaporated

出典と根拠

ORDレコード
ord-49b392f28f494bed8baf1f129c963479
出典データセット
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07432255B2

反応ノート

読み込み中…

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