HCID 56615476, compound → HCID 15610185, compound

HRID 2057437Notes

Reaction equation

HRID 2057437 reaction equation
[CH2:1]([CH:4]1[CH2:15][CH:14]=[CH:13][CH2:12][CH2:11][CH:10]=[CH:9][CH2:8][CH:7]([CH2:16][CH2:17][CH3:18])[N:6]=[N:5]1)[CH2:2][CH3:3].[H][H]>C(O)(C)(C)C.[Rh]>[NH2:5][CH:4]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH:7]([NH2:6])[CH2:16][CH2:17][CH3:18])[CH2:1][CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 56615476HCID 56615476, compoundHCID 178418361HCID 178418361, compound3×

Product 1

HCID 15610185HCID 15610185, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 6386tert-ButanolSolvent

Procedure

942 g (3.79 moles) of 3,12-dipropyl-1,2-diaza-1,5,9-cyclododecatriene (diastereoisomer mixture) are dissolved in a stirred autoclave in 3800 ml of tert-butanol. After addition of 90 g of a rhodium/alumina catalyst (5% by weight), hydrogen is introduced up to a pressure of 130-150 bar and hydrogenation is effected at 150°-180° C. until the uptake of hydrogen is complete. After cooling, excess hydrogen is blown off, the suspension is sucked from the autoclave and the catalyst is collected by suction over a small amount of hyflo (filter aid). The filtrate is concentrated by rotary evaporation and the product is purified by distillation, yielding as main fraction 462 g (48% of theory) of 4,13-diaminohexadecane as a colourless oil [b.p. 132°-135° C./0.01 torr; nD20. 1.4590; IR spectrum (liquid) includes bands at 3278 and 1613 cm-1 ].

Workup

  1. additionis introduced up to a pressure of 130-150 bar and hydrogenation
  2. temperatureAfter cooling
  3. customthe catalyst is collected by suction over a small amount of hyflo (filter aid)
  4. concentrationThe filtrate is concentrated by rotary evaporation
  5. distillationthe product is purified by distillation

Sources & evidence

ORD record
ord-c720ebe3506b4b768b37c007bf9f8d98
Source dataset
uspto-grants-1980_07
Patent number
US04210743

Reaction notes

Loading…