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

HRID 1921068Notes

Reaction equation

HRID 1921068 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].CCN(CC)CC.[C:21](Cl)(=[O:24])[CH:22]=[CH2:23]>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:21](=[O:24])[CH:22]=[CH2:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 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 stirred solution of 1-methyl-2-(methylaminomethyl)-1H-indole (13 g, 8.6 mmole) and Et3N (1.35 mL, 9.6 mmole) in CH2Cl2 (75 mL) at 0° C. was added dropwise acryloyl chloride (0.77 mL, 93 mmole) over 5 minutes. After 2 h the reaction was washed with cold H2O, brine, dried (MgSO4) and concentrated under vacuum. The residue was used without further purification.

Workup

  1. washAfter 2 h the reaction was washed with cold H2O, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under vacuum
  4. customThe residue was used without further purification

Sources & evidence

ORD record
ord-4f45d389663b46ba887ae2742122d8cd
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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