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

HRID 597820

反応式

HRID 597820 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d8bbc063d5a14a22b31ca1bada1a2617
出典データセット
uspto-grants-2011_03
特許番号
US07897594B2

関連ノート

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