Sodium Carbonate → 1-[5-Benzoyl-3-(pyridin-4-yl)thiophen-2-yl]piperidin-4-one

HRID 1869180ノート

反応式

HRID 1869180 の反応式
O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[S:15][C:14]([C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[O:17])=[CH:13][C:12]=3[C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[CH2:7][CH2:6]2)[O:4]CC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O.CC(C)=O>[C:16]([C:14]1[S:15][C:11]([N:8]2[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]2)=[C:12]([C:24]2[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=2)[CH:13]=1)(=[O:17])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 16093274HCID 16093274、化合物

生成物 1

HCID 160932771-[5-Benzoyl-3-(pyridin-4-yl)thiophen-2-yl]piperidin-4-one収率 63%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒2 回

実験手順

A solution of [5-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-4-pyridin-4-yl-thiophen-2-yl]-phenyl-methanone (39.5 mg, 0.097 mmole), p-toluenesulfonic acid monohydrate (37 mg, 0.194 mmole, 2 eq.), acetone (2 mL), and water (1 mL) was heated to reflux overnight. The solution was diluted with water and made basic to pH 14 with 4N sodium hydroxide or 1 M sodium carbonate solution. The solution was extracted twice with ethyl acetate. The organic extracts were dried over magnesium sulfate, filtered, and purified by column chromatography to provide the product as yellow solid (22 mg, 63%). 1H NMR (CDCl3) δ 8.61 (m, 2H), 7.81-7.45 (m, 8H), 3.46 (m, 4H), 2.52 (m, 4H). MS (m/z): 363 (MH+), 385 (MNa+).

後処理

  1. temperatureto reflux overnight
  2. extractionThe solution was extracted twice with ethyl acetate
  3. dry with materialThe organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. custompurified by column chromatography

出典と根拠

ORDレコード
ord-24f2e851f40843e5ab57ed9a6913b2c5
出典データセット
uspto-grants-2009_12
特許番号
US07638525B2

反応ノート

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