Sodium Carbonate → Trans-N-(2H-1-benzopyran-4-yl-methyl)-N-methyl-cinnamylamine

HRID 851161Notes

Reaction equation

HRID 851161 reaction equation
[CH2:1]([NH:10][CH3:11])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[CH2:13][C:14]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[O:17][CH2:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[O:17]1[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:14]([CH2:13][N:10]([CH2:1]/[CH:2]=[CH:3]/[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH3:11])=[CH:15][CH2:16]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 6387604N-MethylcinnamylamineHCID 133927154-chloromethyl-2H-1-benzopyrane

Product 1

HCID 13392716Trans-N-(2H-1-benzopyran-4-yl-methyl)-N-methyl-cinnamylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.15 g of trans-N-cinnamyl-methylamine in 20 ml of dimethylformamide are slowly added dropwise with stirring to 1.4 g of 4-chloromethyl-2H-1-benzopyrane and 0.8 g of sodium carbonate in 40 ml dimethylformamide. Stirring is continued for 24 hours at room temperature, the resulting mixture evaporated under vacuum and the residue taken up in ethylacetate/water. The organic phase is separated, washed with 1% tartaric acid, saturated NaHCO3 and saturated NaCl, dried over MgSO4 and concentrated by evaporation. After purification by chromatography on kieselgel (eluant toluene/ethylacetate 10/1) the title compound is obtained.

Workup

  1. customthe resulting mixture evaporated under vacuum
  2. customThe organic phase is separated
  3. washwashed with 1% tartaric acid, saturated NaHCO3 and saturated NaCl
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated by evaporation
  6. customAfter purification by chromatography on kieselgel (eluant toluene/ethylacetate 10/1) the title compound
  7. customis obtained

Sources & evidence

ORD record
ord-1d2b79bb0d1047129aa2d0dc8f0e25f1
Source dataset
uspto-grants-1983_05
Patent number
US04382951

Reaction notes

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