Water → 1-(3-(2-(1-Benzothiophene-5-yl)ethoxy)propyl)-3-pyrrolidinol

HRID 597820

반응식

HRID 597820 반응식
Cl[CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[S:15][CH:14]=[CH:13][C:12]=2[CH:16]=1.[NH:17]1[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[S:15]1[C:11]2[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][O:5][CH2:4][CH2:3][CH2:2][N:17]3[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18]3)=[CH:16][C:12]=2[CH:13]=[CH:14]1

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 982104-HydroxypyrrolidineHCID 219900695-[2-(3-Chloropropyloxy)ethyl]benzo[b]thiophene

생성물 1

HCID 219900371-(3-(2-(1-Benzothiophene-5-yl)ethoxy)propyl)-3-pyrrolidinol수율 54.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
85 °C

실험 절차

1.20 g of 5-(2-(3-chloropropoxy)ethyl)-1-benzothiophene was dissolved in 12 ml of N,N-dimethylformamide. Thereafter, 0.82 g of 3-pyrrolidinol and 1.30 g of potassium carbonate were added to the obtained solution, and the mixture was then stirred at 85° C. for 2.5 hours. After the reaction mixture was cooled, water and ethyl acetate were added thereto, and an organic layer was separated. The organic layer was successively washed with water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. Thereafter, the solvent was distilled away under a reduced pressure. The residue was purified by column chromatography (eluent; chloroform:methanol=20:1 to 10:1), so as to obtain 0.78 g of an achromatic oil product, 1-(3-(2-(1-benzothiophene-5-yl)ethoxy)propyl)-3-pyrrolidinol.

후처리

  1. temperatureAfter the reaction mixture was cooled
  2. customan organic layer was separated
  3. washThe organic layer was successively washed with water
  4. dry with materiala saturated saline solution, and then dried over anhydrous magnesium sulfate
  5. distillationThereafter, the solvent was distilled away under a reduced pressure
  6. customThe residue was purified by column chromatography (eluent; chloroform:methanol=20:1 to 10:1)

출처 및 근거

ORD 기록
ord-d8bbc063d5a14a22b31ca1bada1a2617
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897594B2

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