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

HRID 1362327Notes

Reaction equation

HRID 1362327 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[N:5]([CH3:13])[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.[C:14](Cl)(=[O:17])[CH:15]=[CH2:16].CCN(CC)CC>C(Cl)Cl>[CH3:1][N:2]([CH2:3][C:4]1[N:5]([CH3:13])[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:14](=[O:17])[CH:15]=[CH2:16]

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]acrylamideYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl-(1-methyl-1H-indol-2-ylmethyl)amine (2.00 g, 11.5 mmol) in CH2Cl2 (100 mL) was treated with acryloyl chloride (1.03 mL, 12.7 mmol) followed by Et3N (1.8 mL, 13 mmol). After stirring for 2 h, the solution was diluted with CH2Cl2 (100 mL) and washed with saturated aqueous NaHCO3 (200 mL). The aqueous layer was extracted with CH2Cl2 (200 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated to an orange oil. Purification by flash column chromatography (silica gel, CH2Cl2/MeOH, 99.5:0.5 to 99:1) gave the title compound (2.10 g, 80%) as a tan oil: 1H NMR (300 MHz, CDCl3) δ 7.59-7.56 (m, 1H), 7.32-7.19 (m, 2H), 7.13-7.08 (m, 1H), 6.66-6.57 (m, 1H), 6.47-6.38 (m, 2H), 5.78-5.74 (m, 1H), 4.88-4.74 (m, 2H), 3.69 (s, 3H), 3.06-2.97 (m, 3H); MS (ESI) m/e 229 (M+H)+.

Workup

  1. washwashed with saturated aqueous NaHCO3 (200 mL)
  2. extractionThe aqueous layer was extracted with CH2Cl2 (200 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to an orange oil
  6. customPurification by flash column chromatography (silica gel, CH2Cl2/MeOH, 99.5:0.5 to 99:1)

Sources & evidence

ORD record
ord-9d1fb30b3a3e4e44aa03234543796510
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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