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

HRID 1791507

반응식

HRID 1791507 반응식
[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]

참가 물질

5

반응물 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 249055-Bromoindole

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9299ce90a014458f90c0ed8e50ecd9e9
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074817B2

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