Triethylamine → HCID 59277536, compound

HRID 2097066Notes

Reaction equation

HRID 2097066 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[O:5][C:6]2[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=2[C:8]=1[CH2:9][CH2:10][CH3:11].[C:16](Cl)(=[O:19])[CH:17]=[CH2:18].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][N:2]([CH2:3][C:4]1[O:5][C:6]2[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=2[C:8]=1[CH2:9][CH2:10][CH3:11])[C:16](=[O:19])[CH:17]=[CH2:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 59277583HCID 59277583, compound

Product 1

HCID 59277536HCID 59277536, compoundYield 104.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl-(3-propyl-benzofuran-2-ylmethyl)amine (1.10 g, 5.41 mmol) in CH2Cl2 (40 mL) was treated with acryloyl chloride (0.45 mL, 5.68 mmol) and triethylamine (1.5 mL, 10.8 mmol). The mixture was stirred at room temperature for 2 h. The solution was washed with water and brine, dried (Na2SO4), filtered and concentrated under reduced pressure to give the title compound (1.46 g, 99%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 7.59 (d, J=5.4 Hz, 1H), 7.49 (d, J=7.5 Hz, 1H), 7.28-7.15 (m, 2H), 6.89-6.70 (m, 1H), 6.20 (t, J=2.4 Hz, 1H), 5.75 (t, J=4.5 Hz, 1H), 4.83-4.71 (m, 2H), 3.33-3.07 (m, 2H), 2.87-2.67 (m, 3H), 1.65-1.58 (m, 2H), 0.95-0.88 (m, 3H); ESI MS m/z 258 (M+H)+.

Workup

  1. washThe solution was washed with water and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4a66e465cb7b4fb79c4d35848612915f
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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