Dimethylformamide → HCID 131728950, compound

HRID 1478660Notes

Reaction equation

HRID 1478660 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6]CN.[C:12](=[O:15])([O-:14])[O-].[Cs+].[Cs+].[CH2:18](Br)[CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH3:28][N:29](C=[O:32])C>O>[C:3]([OH:2])(=[O:32])/[CH:11]=[CH:10]/[C:12]([OH:14])=[O:15].[CH3:1][O:2][C:3]1[C:4]2[CH:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:19][CH2:18][N:29]([CH3:28])[CH2:6][C:5]=2[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 748663-MethoxyphenethylamineHCID 98116Bromomethylstyrene

Product 1

HCID 131728950HCID 131728950, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of (3-methoxybenzyl)methylamine (3.02 g, 20 mmol) and cesium carbonate (7.82 g, 24 mmol) in DMF (50 mL) was added cinnamyl bromide (4.47 g, 22 mmol). The reaction mixture was stirred at room temperature for 15 hours. The reaction mixture was diluted with water and extracted with 1:1 hexanes/ethyl acetate (3×). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated to provide the desired product (3.1 g, 58%): 1H NMR (CDCl3, 500 MHz) δ 7.39-7.37 (m, 2H), 7.32-7.29 (m, 2H), 7.23-7.20 (m, 2H), 6.93-6.91 (m, 2H), 6.81-6.78 (m, 1H), 6.54 (d, J=15.9 Hz, 1H), 6.31 (dt, J=15.9, 6.6 Hz, 1H), 3.81 (s, 3H), 3.52 (s, 2H), 3.19 (dd, J=6.6, 1.2 Hz, 2H), 2.25 (s, 3H); ESI MS m/z=268 [M+H]+. This crude product was used in the next step without further purification.

Workup

  1. extractionextracted with 1:1 hexanes/ethyl acetate (3×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3e614d31c24f416ca3a1f8d83c13eaa9
Source dataset
uspto-grants-2016_08
Patent number
US09403776B2

Reaction notes

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