Benzylamine → 2-Propenamide, 3,3-bis(4-methoxyphenyl)-N-(phenylmethyl)-

HRID 1591360Notes

Reaction equation

HRID 1591360 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:10][C:11]([OH:13])=O)=[CH:5][CH:4]=1.C(N(CC)CC)C.C(Cl)(=O)OCC.[CH2:35]([NH2:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CN(C)C=O.C(OCC)(=O)C>[CH2:35]([NH:42][C:11](=[O:13])[CH:10]=[C:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 12660800HCID 12660800, compound

Product 1

HCID 30876662-Propenamide, 3,3-bis(4-methoxyphenyl)-N-(phenylmethyl)-

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.84 g (0.01M) of 3,3-bis(4-methoxyphenyl)acrylic acid was dissolved in 10 ml of dimethylformamide. To the obtained solution, 1.2 g (0.012M) of triethylamine and 1.2 g of ethyl chlorocarbonate were added under icecooling. After one hour, 1.2 g of benzylamine was added thereto and the mixture was stirred at room temperature for one hour. After the completion of the reaction, the reaction mixture was dissolved in 50 ml of ethyl acetate, washed with 10% hydrochloric acid, a saturated aqueous solution of NaHCO3 and a saline solution successively and dried over magnesium sulfate followed by purifying by silica gel column chromatography. Thus 3.3 g of the title compound having the following physicochemical properties was obtained.

Workup

  1. customAfter the completion of the reaction
  2. washwashed with 10% hydrochloric acid
  3. dry with materiala saturated aqueous solution of NaHCO3 and a saline solution successively and dried over magnesium sulfate
  4. customby purifying by silica gel column chromatography
  5. customwas obtained

Sources & evidence

ORD record
ord-cc8c81c696784b3d85ff112a4a380d9a
Source dataset
uspto-grants-1993_04
Patent number
US05206403

Reaction notes

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