Dimethylamine → Indole, 5-bromo-3-(dimethylamino)methyl-

HRID 1791507

反応式

HRID 1791507 の反応式
[CH3:1][NH:2][CH3:3].[CH2:4]=O.[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2>C(O)(=O)C>[Br:6][C:7]1[CH:8]=[C:9]2[C:3](=[CH:14][CH:15]=1)[NH:2][CH:1]=[C:10]2[CH2:11][N:12]([CH3:4])[CH3:13]

参加物

5

反応物 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 249055-Bromoindole

生成物 1

HCID 13249Indole, 5-bromo-3-(dimethylamino)methyl-収率 88.7%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a mixture of 40% aqueous dimethylamine (5.95 g, 52.8 mmol), 37% aqueous formaldehyde (4.21 g, 51.9 mmol) and acetic acid (7 mL) was added 5-bromo-1H-indole (9.79 g, 49.9 mmol). The reaction mixture was stirred for 21 hours at room temperature and poured into a 2.5 N sodium hydroxide/ice mixture (200 mL). This was extracted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and evaporated to dryness. It was dried at 60° C. for 30 minutes to yield (5-bromo-1H-indol-3-ylmethyl)-dimethyl-amine (11.2 g) as a brown solid: mp 160-162° C. 1HNMR (200 MHz, DMSO-d6): δ 11.1 (br s, 1H), 7.75 (s, 1H), 7.15-7.35 (m, 3H), and 3.5 ppm (s, 2H).

後処理

  1. extractionThis was extracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness
  5. customIt was dried at 60° C. for 30 minutes

出典と根拠

ORDレコード
ord-9299ce90a014458f90c0ed8e50ecd9e9
出典データセット
uspto-grants-2006_07
特許番号
US07074817B2

関連ノート

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