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

HRID 1791507

Reaction equation

HRID 1791507 reaction equation
[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]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 249055-Bromoindole

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-9299ce90a014458f90c0ed8e50ecd9e9
Source dataset
uspto-grants-2006_07
Patent number
US07074817B2

Linked notes

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