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Acetic Acid → 8-{4-[4-(1H-indole-4-yl)-1-piperazinyl]-1-piperidinyl}quinoline

HRID 2241971
ノート
印刷プレビュー

反応式

HRID 2241971 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N:11]2[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]2)[CH:4]=[CH:3][CH:2]=1.[N:18]1([C:24]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:25]=2[CH:26]=[CH:27][NH:28]3)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[NH:28]1[C:29]2[C:25](=[C:24]([N:18]3[CH2:23][CH2:22][N:21]([CH:14]4[CH2:15][CH2:16][N:11]([C:9]5[CH:8]=[CH:7][CH:6]=[C:5]6[C:10]=5[N:1]=[CH:2][CH:3]=[CH:4]6)[CH2:12][CH2:13]4)[CH2:20][CH2:19]3)[CH:32]=[CH:31][CH:30]=2)[CH:26]=[CH:27]1
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 176Acetic AcidHCID 5945904-(piperazin-1-yl)-1H-indoleHCID 5049666Sodium triacetoxyborohydrideHCID 592048421-Quinolin-8-yl-piperidin-4-one

生成物 1

HCID 120042838-{4-[4-(1H-indole-4-yl)-1-piperazinyl]-1-piperidinyl}quinoline収率 40.8%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

To a solution of 0.270 g of 1-quinolin-8-yl-piperidin-4-one (Example A, Step 6, above) and 0.240 g of 4-piperazino-indole (commercially available) in 15 mL CH2Cl2 was added 0.327 g of sodium triacetoxyborohydride and 0.2 mL acetic acid. The reaction was stirred at room temperature overnight. It was quenched with 1N NaOH, and the product was extracted with CH2Cl2. The organic phase was washed with water, dried over magnesium sulfate and evaporated. The product crystallized to give 0.200 g of the desired product. Mp: 256° C.; MS (ES) m/z (relative intensity): 412 (M++−H, 100).

後処理

  1. customIt was quenched with 1N NaOH
  2. extractionthe product was extracted with CH2Cl2
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe product crystallized

出典と根拠

ORDレコード
ord-93c30f2efedf4440930022e387a7a6f5
出典データセット
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07671056B2

反応ノート

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