Diethyl Ether → HCID 23459455, compound

HRID 2287127Notes

Reaction equation

HRID 2287127 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.[C:16]1([C:22]2([CH2:28][C:29]#[N:30])[CH:27]=[CH:26][CH2:25][CH:24]=[CH:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[C:16]1([C:22]2([CH2:28][CH2:29][NH2:30])[CH:27]=[CH:26][CH2:25][CH:24]=[CH:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 23459446HCID 23459446, compound

Product 1

HCID 23459455HCID 23459455, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.68 g. of aluminum trichloride and 0.24 g. of lithium aluminum hydride are placed in 8 ml. of absolute ether. 1 g. of 1-phenyl-2,5-cyclohexadien-1-acetonitrile in 5 ml. of absolute ether is added dropwise while stirring. After stirring at room temperature for 2 hours, the mixture is worked-up as follows: The mixture is treated with 1 ml. of water and 25 ml. of 3 N aqueous sodium hyroxide, filtered under suction and the filter rinsed with ether. After separating the phases, the organic phase is dried over sodium sulfate, filtered and concentrated to dryness. The crude product obtained is chromatographed on 50 g. of Alox (neutral), educt being first of all eluted with ether and then end product being eluted with methylene chloride/methanol (10:1). There is obtained 1-phenyl-2,5-cyclohexadien-1-ethylamine as an oily product. 3 g. of this product are converted in the usual manner into the hydrochloride which, after recrystallization from methylene chloride/ether, has a melting point of 170°-172° C.

Workup

  1. stirringAfter stirring at room temperature for 2 hours
  2. additionThe mixture is treated with 1 ml
  3. filtrationof 3 N aqueous sodium hyroxide, filtered under suction
  4. washthe filter rinsed with ether
  5. customAfter separating the phases
  6. dry with materialthe organic phase is dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe crude product obtained
  10. customis chromatographed on 50 g
  11. washall eluted with ether
  12. washbeing eluted with methylene chloride/methanol (10:1)

Sources & evidence

ORD record
ord-39f5091157ff43ddb8164eb37cf2ad3e
Source dataset
uspto-grants-1981_05
Patent number
US04269788

Reaction notes

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