Water → HCID 9884572, compound

HRID 1698841Notes

Reaction equation

HRID 1698841 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:18]([C:26]1[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28](Cl)=[O:29])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>C1(C)C=CC=CC=1>[OH:25][C:18]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:26]2[C:27](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:28](=[O:29])[N:10]1[CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5610TyramineHCID 8471TriethylamineHCID 109992952-benzoylbenzoyl chloride

Product 1

HCID 9884572HCID 9884572, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

At room temperature, 1.46 g (10.63 mmol) of 2-(4-hydroxy-phenyl)ethylamine and 1.08 g (10.63 mmol) of triethylamine in 30 ml of absolute toluene were admixed dropwise with a solution of 2.0 g (8.17 mmol) of 2-benzoylbenzoyl chloride in 20 ml of absolute toluene. The reaction mixture was heated under reflux for 3 h and cooled, and the turbid solution was admixed with 20 ml of water. The organic phase was separated off, washed three times with 1 M aqueous hydrochloric acid and evaporated to dryness using a rotary evaporator. The solid residue was purified by column chromatography on silica gel 60. Elution was carried out using a toluene/ethyl acetate gradient (0 to 20% ethyl acetate). The product-containing fractions were evaporated to dryness using a rotary evaporator. The residue was suspended in diethyl ether and filtered off with suction. Yield: 0.21 g. M.p.: 188° C.

Workup

  1. customAt room temperature
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 3 h
  4. temperaturecooled
  5. customThe organic phase was separated off
  6. washwashed three times with 1 M aqueous hydrochloric acid
  7. customevaporated to dryness
  8. customa rotary evaporator
  9. customThe solid residue was purified by column chromatography on silica gel 60
  10. washElution
  11. customThe product-containing fractions were evaporated to dryness
  12. customa rotary evaporator
  13. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-744771d7f3c64f56ae98fc54f6dfe0a2
Source dataset
uspto-grants-2002_02
Patent number
US06344468B1

Reaction notes

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