O-Methyltyramine → HCID 70227909, compound

HRID 1976901Notes

Reaction equation

HRID 1976901 reaction equation
CN(C)C=O.[N+](C1C=CC(O[C:16](=[O:28])/[C:17](/[CH3:27])=[CH:18]/[C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[NH2:26])=CC=1)([O-])=O.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][NH2:39])=[CH:33][CH:32]=1>C(Cl)Cl.CO.C(OCC)(=O)C.O>[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][NH:39][C:16](=[O:28])[C:17]([CH3:27])=[CH:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[NH2:26])=[CH:33][CH:32]=1

Participants

7

Reactant 3

HCID 4657O-MethyltyramineHCID 6228DimethylformamideHCID 12070499HCID 12070499, compound

Product 1

HCID 70227909HCID 70227909, compoundYield 91.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

Into 2 ml of dimethylformamide, 0.20 g (0.60 mmol) of (E)3-(2-amino-4-chlorophenyl)-2-methyl-2-propenoic acid p-nitrophenyl ester and 0.11 g (0.72 mmol) of 2-( 4-methoxyphenyl)ethylamine (manufactured by Wako Pure Chemical Industries, Ltd.) were dissolved, and the mixture was reacted for 20 hours at room temperature. After the completion of the reaction was verified by TLC, ethyl acetate and water were added thereto. The resulting ethyl acetate layer was fractionated, and was washed several times with a 5% aqueous sodium hydrogencarbonate solution and then with a saturated aqueous sodium chloride solution. The washed solution was dried with magnesium sulfate anhydride, and the solvent was evaporated under a reduced pressure. The crude product obtained here was refined by a silica gel column chromatography (developing solvent: methylene chloride/methanol=95/5), whereby 0.19 g of the aimed compound was obtained (yield: quantitative).

Workup

  1. customthe mixture was reacted for 20 hours at room temperature
  2. additionwere added
  3. washwas washed several times with a 5% aqueous sodium hydrogencarbonate solution
  4. dry with materialThe washed solution was dried with magnesium sulfate anhydride
  5. customthe solvent was evaporated under a reduced pressure
  6. customThe crude product obtained here

Sources & evidence

ORD record
ord-f55387573dcf4a62b8393b246aec4da1
Source dataset
uspto-grants-2001_05
Patent number
US06229020B1

Reaction notes

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