Piperidine → HCID 54352759、化合物

HRID 2120239

反応式

HRID 2120239 の反応式
[OH:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][C:7](=[O:13])[NH:8]2.[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][C:17]=1[C:24]1[S:25][CH:26]=[CH:27][CH:28]=1.N1CCCCC1>C(O)C>[OH:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[CH:20][C:19]1[CH:22]=[CH:23][C:16]([O:15][CH3:14])=[C:17]([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)[CH:18]=1)[C:7](=[O:13])[NH:8]2

参加物

5

反応物 3

HCID 8082PiperidineHCID 109430044-(2-Hydroxyethyl)indolin-2-oneHCID 219810244-Methoxy-3-(thiophen-2-yl)benzaldehyde

生成物 1

HCID 54352759HCID 54352759、化合物収率 47%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (1.6 g, 9.2 mmol), 4-methoxy-3-thiophen-2-yl-benzaldehyde (2 g, 9.2 mmol) and piperidine (4.5 mL, 85 mmol) in ethanol (46 mL) was heated to reflux for overnight. The reaction mixture was concentrated and the residue was chromatographed on a column of silica gel to give 1.63 g (47%) of 4-(2-hydroxy-ethyl)-3-(4-methoxy-3-thiophen-2-yl-benzylidene)-1,3-dihydro-indol-2-one as a yellow orange solid. 1HNMR (300 MHz, DMSO-d6) δ 10.53 (s, br, 1H, NH), 8.73 (d, J=2.1 Hz, 1H), 8.10 (dd, J=2.2 & 9.1 Hz, 1H), 7.74 (s, 1H, H-vinyl), 7.56-7.65 (m, 2H), 7.07-7.22 (m, 3H), 6.81 (d, J=7.5 Hz, 1H), 6.68 (dd, J=0.6, 7.5 Hz, 1H), 4.87 (t, J=4.5 Hz, 1H, OH), 3.97 (s, 3H, OCH3), 3.68-3.75 (m, 2H, CH2CH2OH), 3.09 (t, J=4.5 Hz, 2H, CH2CH2OH).

後処理

  1. temperaturewas heated
  2. temperatureto reflux for overnight
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was chromatographed on a column of silica gel

出典と根拠

ORDレコード
ord-026f27878bb8434eb2bd152067b6cb4c
出典データセット
uspto-grants-2004_02
特許番号
US06689806B1

関連ノート

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