Dimethyl Sulfoxide → (1-Benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanone

HRID 914856노트

반응식

HRID 914856 반응식
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([N:18]1[CH2:23][CH2:22][CH:21]([CH:24]([CH:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][O:27]2)[OH:25])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[CH2:11]([N:18]1[CH2:19][CH2:20][CH:21]([C:24]([CH:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][O:27]2)=[O:25])[CH2:22][CH2:23]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22248465(1-Benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanol

생성물 1

HCID 22248144(1-Benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanone수율 87.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

After adding 0.511 ml of dimethylsulfoxide dropwise to a dichloromethane solution (15 ml) containing 0.315 ml of oxalyl chloride at −70° C., the mixture was stirred for 10 minutes, a solution of 597 mg of (1-benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanol in dichloromethane (5 ml) was added dropwise, and stirring was continued for 1 hour. Next, 2.5 ml of triethylamine was added dropwise to the reaction solution, the cooling bath was removed, and the mixture was stirred at room temperature. Water was added to the reaction solution, and extraction was performed with ethyl acetate. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain the title compound (517 mg, 33% yield).

후처리

  1. stirringstirring
  2. waitwas continued for 1 hour
  3. customthe cooling bath was removed
  4. stirringthe mixture was stirred at room temperature
  5. additionWater was added to the reaction solution, and extraction
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-a3d861881ba347609a29246b82287887
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265108B2

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