Hydrochloric Acid → [5-(2-methoxy-ethoxy)-1H-indol-ylmethyl]-dimethyl-amine

HRID 41060

反応式

HRID 41060 の反応式
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2.[CH2:15]=O.Cl.[CH3:18][NH:19][CH3:20]>C(O)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:18][N:19]([CH3:15])[CH3:20])[CH:10]=[CH:9]2

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 103525375-(2-methoxyethoxy)-1H-indole

生成物 1

HCID 66938466[5-(2-methoxy-ethoxy)-1H-indol-ylmethyl]-dimethyl-amine収率 90%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A solution of 5-(2-methoxy-ethoxy)-indole (2.06 g, 11.0 mmol) in acetic acid (7 ml) and 40% aqueous dimethylamine (2.1 ml) is cooled to 0° C., and 36% aqueous formaldehyde (1.38 ml) (pre-cooled to 0° C.) is added drop wise. The mixture is stirred at room temperature overnight, 2 M hydrochloric acid is added, and the mixture is washed with dichloromethane. The aqueous layer is made alkaline with 10% NaOH, and is extracted with dichloromethane. The combined organic layer is washed with water, is dried and concentrated. The residue is purified by column chromatography (dichloromethane-methanol, 4:1→dichloromethane-methanol-water-aqueous ammonia, 10:20:1:1) to afford [5-(2-methoxy-ethoxy)-1H-indol-ylmethyl]-dimethyl-amine (2.42 g, 90%). M.p. 163-164° C. (from toluene-N,N-dimethylformamide).

後処理

  1. washthe mixture is washed with dichloromethane
  2. extractionis extracted with dichloromethane
  3. washThe combined organic layer is washed with water
  4. customis dried
  5. concentrationconcentrated
  6. customThe residue is purified by column chromatography (dichloromethane-methanol, 4:1→dichloromethane-methanol-water-aqueous ammonia, 10:20:1:1)

出典と根拠

ORDレコード
ord-647412664e524dd98d16f3f196ff2ed6
出典データセット
uspto-grants-2013_09
特許番号
US08530493B2

関連ノート

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