Ammonia → 2-[3-(2-Aminoethyl)phenyl]ethanamine

HRID 1757481

Reaction equation

HRID 1757481 reaction equation
[C:1]1([CH2:10][C:11]#[N:12])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]#[N:9])[CH:2]=1.N>[Ni].C(O)C>[NH2:9][CH2:8][CH2:7][C:3]1[CH:4]=[CH:5][CH:6]=[C:1]([CH2:10][CH2:11][NH2:12])[CH:2]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 693751,3-Benzenediacetonitrile

Product 1

HCID 27496402-[3-(2-Aminoethyl)phenyl]ethanamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 25.0 g (0.16 mmol) meta-xylylene dicyanide, 300 ml ethanol and50 ml conc. NH3 is hydrogenated in the presence of Raney nickel for 5 hrs. at 100° C. and 150 bar. One then filters off with suction and evaporates. The residue is dissolved in ether, the solution is clarified with active carbon and finally mixed with HCl-containing ether, whereby the dihydrochloride precipitates out. One filters off with suction, washeswith ether and dries. Yield 23.2 g (61% of theory) of dihydrochloride with the m.p. 282°-286° C.

Workup

  1. customat 100° C.
  2. customevaporates
  3. dissolutionThe residue is dissolved in ether
  4. additionfinally mixed with HCl-
  5. additioncontaining ether, whereby the dihydrochloride
  6. customprecipitates out

Sources & evidence

ORD record
ord-4f321a6bab234c8699274f46ff041bbd
Source dataset
uspto-grants-1995_08
Patent number
US05446065

Linked notes

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