1-Butene → HCID 19779547, compound

HRID 2082097Notes

Reaction equation

HRID 2082097 reaction equation
[CH2:1]([C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Al].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:20]=[CH:21][CH2:22][CH3:23]>CCOCC>[CH:21]([C:13]1[CH:14]=[C:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:9]=[C:10]([CH:1]([CH2:2][CH3:3])[CH3:8])[C:11]=1[NH2:12])([CH2:22][CH3:23])[CH3:20]

Participants

6

Reactant 4

HCID 78441-ButeneHCID 136914Benzenamine, 4-(phenylmethyl)-HCID 5359268AluminumHCID 6451240Aluminum(III) Chloride

Product 1

HCID 19779547HCID 19779547, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

81 g of 4-benzylaniline, 1.2 g of aluminium powder, 3.6 g of anhydrous aluminium chloride and 100 g of but-1-ene are heated for 24 hours at +260° C. in an autoclave. After cooling, the reaction mass is poured into ice-cold dilute sodium hydroxide solution and taken up in ether. The ether phase is separated off, dried over sodium sulfate and subjected to fractional distillation; b.p. 130°-134° C./0.03 torr. Chromatographic purification on silica gel using hexane/ethyl acetate as eluant affords the title compound of formula ##STR12## in the form of a colourless oil; refractive index nD24 : 1.5579.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mass is poured into ice-cold dilute sodium hydroxide solution
  3. customThe ether phase is separated off
  4. dry with materialdried over sodium sulfate
  5. distillationsubjected to fractional distillation
  6. customChromatographic purification on silica gel

Sources & evidence

ORD record
ord-d6e3be731f974882965aff2107ae1cf3
Source dataset
uspto-grants-1993_02
Patent number
US05187197

Reaction notes

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