Triethylamine → (R)-N-methyl-N-[1-(3-methyl-benzofuran-2-yl)-ethyl]acrylamide

HRID 1879964Notes

Reaction equation

HRID 1879964 reaction equation
[CH3:1][NH:2][C@@H:3]([C:5]1[O:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]=1[CH3:10])[CH3:4].CCN(CC)CC.[C:22](Cl)(=[O:25])[CH:23]=[CH2:24]>CN(C=O)C.O>[CH3:1][N:2]([C@@H:3]([C:5]1[O:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]=1[CH3:10])[CH3:4])[C:22](=[O:25])[CH:23]=[CH2:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 55276559(R)-N-methyl-1-(3-methylbenzofuran-2-yl)ethanamine

Product 1

HCID 59332837(R)-N-methyl-N-[1-(3-methyl-benzofuran-2-yl)-ethyl]acrylamideYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To an ice cold mixture of (R)-methyl-[1-(3-methyl-benzofuran-2-yl)-ethyl]amine (7.5 mL of a 0.46 M solution in DMF, 3.5 mmol) and Et3N (0.6 mL, 4.1 mmol) was added acryloyl chloride (0.3 mL, 3.8 mmol) drop-wise. The mixture was slowly warmed to room temperature and stirred overnight. The mixture was diluted with H2O and extracted with Et2O (3×). The combined organics were washed with H2O and satd NaCl, dried (Na2SO4) and concentrated. Purification by column chromatography (silica gel, 7:3 hexanes/EtOAc) gave the title compound (630 mg, 75%) as a yellow oil: 1H NMR (300 MHz, DMSO-d6) 7.50-7.47 (m, 1H), 7.44-7.41 (m, 1H), 7.30-7.20 (m, 2H), 6.81-6.52 (m, 1H), 6.40-6.25 (m, 2H), 5.74-5.70 (m, 1H), 2.99-2.90 (m, 3H), 2.23 (s, 3H), 1.69-1.58 (m, 3H).

Workup

  1. extractionextracted with Et2O (3×)
  2. washThe combined organics were washed with H2O and satd NaCl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification by column chromatography (silica gel, 7:3 hexanes/EtOAc)

Sources & evidence

ORD record
ord-729e6bc2f48d45ac9a4c82355562f0e9
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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