Ammonia → 1-Phenylpropane-1,3-diamine

HRID 1701478Notes

Reaction equation

HRID 1701478 reaction equation
[C:1]1([CH:7]2[NH:11][N:10]=[CH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N>CO.[Ni]>[C:1]1([CH:7]([NH2:11])[CH2:8][CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 1208415-Phenyl-4,5-dihydro-1H-pyrazole

Product 1

HCID 130345451-Phenylpropane-1,3-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

73 g (0.5 mol) of 5-phenyl-2-pyrazoline are hydrogenated in 400 ml of methanol saturated with ammonia with 10 g of freshly prepared Raney nickel for 5 hours at 80° C./100 atmospheres. The Raney nickel is filtered off on a suction filter containing a layer of kieselguhr. The solvent is removed from the filtrate in a rotary evaporator and the residue is distilled in a simple distillation apparatus and then through a 25 cm Vigreux column. This gives 66 g=88% of theory of a colourless oil with a boiling point under 0.0004 mm of 73° C. (literature: boiling point under 21 mm, 138°-141° C.).

Workup

  1. filtrationThe Raney nickel is filtered off on a suction
  2. filtrationfilter
  3. additioncontaining a layer of kieselguhr
  4. customThe solvent is removed from the filtrate in a rotary evaporator
  5. distillationthe residue is distilled in a simple distillation apparatus
  6. customunder 0.0004 mm of 73° C. (literature: boiling point under 21 mm, 138°-141° C.)

Sources & evidence

ORD record
ord-ffe58596b840406d82d9fcfb8355d0b2
Source dataset
uspto-grants-1980_03
Patent number
US04193905

Reaction notes

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