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

HRID 1869180노트

반응식

HRID 1869180 반응식
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

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 16093274HCID 16093274, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매2회

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-24f2e851f40843e5ab57ed9a6913b2c5
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07638525B2

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