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

HRID 1029782Notes

Reaction equation

HRID 1029782 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 chromategraphy. 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 chromategraphy
  5. customwas obtained

Sources & evidence

ORD record
ord-efab7f85354a45d5a4db2e3760a377da
Source dataset
uspto-grants-1992_04
Patent number
US05103010

Reaction notes

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