Ammonia → HCID 20521417, compound

HRID 1277863Notes

Reaction equation

HRID 1277863 reaction equation
[H][H].[CH3:3][CH:4]([C:7]([CH3:12])([CH3:11])[CH2:8][C:9]#[N:10])[C:5]#[N:6].N>C(O)C>[CH3:3][CH:4]([C:7]([CH3:12])([CH3:11])[CH2:8][CH2:9][NH2:10])[CH2:5][NH2:6]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 20521420HCID 20521420, compoundHCID 178418361HCID 178418361, compound5×

Product 1

HCID 20521417HCID 20521417, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
105 °C

Procedure

After scavenging with nitrogen and then with hydrogen, commercial hydrogen is introduced under a pressure of 170 atm and then the autoclave is heated to about 105° C. for six hours. Thereafter the autoclave is cooled, the pressure is released and the autoclave is charged with a solution of 68 grams of 2,3,3-trimethylglutaronitrile dissolved in 30 mls abs.ethanol, the scavenging with nitrogen is repeated, there are charged 160 grams of anhydrous ammonia and finally commercial hydrogen is introduced under a pressure of 165 atm approx. The autoclave, which is fitted with a magnetic stirrer, is heated to about 105° C.-108° C. the hydrogen pressure being restored as hydrogen is gradually being absorbed. After about 2 hrs. the pressure does not decrease any more and the above specified temperature is maintained for three additional hours, whereafter the autoclave is allowed to cool. The catalyst is filtered off, the solvent is distilled off and, on the raw production of the reaction, the yield in terms of 2,3,3-trimethyl pentamethylene diamine is determined by gaschromatographic methods in the presence of an internal standard (yield 65%-70%). The diamine is then purified by fractionation and, under a pressure of about 12 Torr. it boils at 105° C.-106° C.

Workup

  1. temperatureThereafter the autoclave is cooled
  2. dissolutiondissolved in 30 mls abs
  3. additionis introduced under a pressure of 165 atm approx
  4. customThe autoclave, which is fitted with a magnetic stirrer
  5. customis gradually being absorbed
  6. temperatureis maintained for three additional hours, whereafter the autoclave
  7. temperatureto cool
  8. filtrationThe catalyst is filtered off
  9. distillationthe solvent is distilled off
  10. customon the raw production of the reaction

Sources & evidence

ORD record
ord-249abc5c6cbe41709778dcd51615fb9f
Source dataset
uspto-grants-1981_07
Patent number
US04279834

Reaction notes

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