Methylamine → N-Methyl-N-[(1-methyl-2-indolyl)methyl]acrylamide

HRID 1710570Notes

Reaction equation

HRID 1710570 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH2:11][NH:12][CH3:13].CN.[C:16](Cl)(=[O:19])[CH:17]=[CH2:18]>C(Cl)Cl>[CH3:13][N:12]([CH2:11][C:3]1[N:2]([CH3:1])[C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:16](=[O:19])[CH:17]=[CH2:18]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 13140Acryloyl chlorideHCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amine

Product 1

HCID 20752825N-Methyl-N-[(1-methyl-2-indolyl)methyl]acrylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-methyl-2-(methylaminomethyl)indole (0.96 g, 5.5 mmole), from Preparation 1, and methylamine (1.54 mL, 11.0 mmole) in CH2Cl2 (50 mL) at 5° C. was added acryloyl chloride (0.48 mL, 6.0 mmole). After 45 min, the reaction solution was poured onto H2O and the layers were separated. The organic phase was dried over Na2SO4 and concentrated to afford the title compound as a yellow oil. This was used directly without further purification.

Workup

  1. additionthe reaction solution was poured onto H2O
  2. customthe layers were separated
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4c8701d5f339450d99743d02041e94e8
Source dataset
uspto-grants-2010_09
Patent number
US07790716B2

Reaction notes

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