Dimethylamine → HCID 2762435, compound

HRID 868838Notes

Reaction equation

HRID 868838 reaction equation
[CH3:1][NH:2][CH3:3].[CH2:4]=O.[CH3:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2.[OH-].[Na+]>C(O)(=O)C>[CH3:1][N:2]([CH3:4])[CH2:3][C:9]1[C:8]2[C:12](=[CH:13][CH:14]=[CH:15][C:7]=2[CH3:6])[NH:11][CH:10]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 852824-Methylindole

Product 1

HCID 2762435HCID 2762435, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a chilled solution of dimethyl amine (30 mL, 40% in water, 120 mmol) and formalin (13 mL, 37% in water, 84 mmol) in glacial acetic acid (30 mL) is added 4-methyl indole (21 g, 165 mmol) at 0° C. The reaction is warmed to room temperature and stirred for 3 hours. The reaction mixture is brought to pH 12 by addition of 50% NaOH and ice, and the product extracted with methylene chloride. The organic layers are dried over Na2SO4 filtered and evaporated in vacuo to give the title compound that is used without further purification (33 g, 162 mmol, 98%) LC/MS (M++1): 205.7.

Workup

  1. extractionthe product extracted with methylene chloride
  2. dry with materialThe organic layers are dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-5e9430295ee14861a44a981cdbca0c98
Source dataset
uspto-grants-2015_03
Patent number
US08969348B2

Reaction notes

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