Benzylamine → HCID 3937474, compound

HRID 2259434Notes

Reaction equation

HRID 2259434 reaction equation
C(N(CC)CC)C.[CH2:8](Cl)[CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O)(=O)/C=C\C(O)=O>O1CCCC1.CC(C)=O>[CH2:8]([NH:25][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 94242Benzene, (3-chloro-1-propenyl)-HCID 444266Maleic Acid

Product 1

HCID 3937474HCID 3937474, compoundYield 44.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

113 ml (818 mmol) of triethylamine were added to 96.4 g (600 mmol) of cinnamyl chloride in 800 ml of tetrahydrofuran, the mixture was heated to 60° C., and then 65.4 ml (600 mmol) of benzylamine were added dropwise. The mixture was refluxed for 3 h and then stirred at room temperature for 15 h. After concentration under water pump vacuum, the contents of the flask were partitioned between methyl t-butyl ether and water (pH=10). The organic phase was washed twice with water, dried with sodium sulfate and concentrated. The crude product (109 g) composed of mono- and bisadduct was dissolved in 400 ml of acetone, a solution of 48 g (413 mmol) of maleic acid in 250 ml of acetone was added while stirring and, after cooling, the precipitated solid was filtered off with suction. After washing with acetone, 60.0 g (30%) of N-cinnamylbenzylamine were isolated as maleate, melting point 169°-170° C.

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. concentrationAfter concentration under water pump vacuum
  3. customthe contents of the flask were partitioned between methyl t-butyl ether and water (pH=10)
  4. washThe organic phase was washed twice with water
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. dissolutionwas dissolved in 400 ml of acetone
  8. stirringwhile stirring
  9. temperatureafter cooling
  10. filtrationthe precipitated solid was filtered off with suction
  11. washAfter washing with acetone

Sources & evidence

ORD record
ord-968c621a98054ce7b17e79ef480a160e
Source dataset
uspto-grants-1995_12
Patent number
US05473080

Reaction notes

Loading…