HCID 56635899, compound → HCID 20231523, compound

HRID 2057438Notes

Reaction equation

HRID 2057438 reaction equation
[CH:1]([CH:4]1[CH2:15][CH:14]=[CH:13][CH2:12][CH2:11][CH:10]=[CH:9][CH2:8][CH:7]([CH:16]([CH3:18])[CH3:17])[N:6]=[N:5]1)([CH3:3])[CH3:2].[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])[CH:16]([CH3:18])[CH3:17])[CH:1]([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 56635899HCID 56635899, compoundHCID 178418361HCID 178418361, compound3×

Product 1

HCID 20231523HCID 20231523, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 6386tert-ButanolSolvent

Procedure

250 g (1 mole) of 3,12-diisopropyl-1,2-diaza-1,5,9-cyclododecatriene (diastereoisomer mixture) are dissolved in 1000 ml of tert -butanol in an agitator autoclave. After addition of 25 g of a rhodium/alumina catalyst (5% by weight of rhodium), hydrogen is introduced up to a pressure of 130 to 150 bar, whereupon hydrogenation is effected at 150° to 180° C. until the hydrogen uptake is complete. After cooling, excess hydrogen is blown off, the suspension is removed from the autoclave by suction and the catalyst is filtered off with suction over a small amount of hyflo (filter aid). The filtrate is concentrated by rotary evaporation and the product is purified by distillation, affording as main fraction 238 g (92% of theory) of 3,12-diamino-2,13-dimethyltetradecane as a colourless oil [b.p. 106°-109° C./0.01 torr; nD20 =1.4600; IR spectrum (in liquid) includes bands at 3355, 3278, 1613 cm-1 ].

Workup

  1. additionis introduced up to a pressure of 130 to 150 bar, whereupon hydrogenation
  2. temperatureAfter cooling
  3. customthe suspension is removed from the autoclave by suction
  4. filtrationthe catalyst is filtered off with suction over a small amount of hyflo (filter aid)
  5. concentrationThe filtrate is concentrated by rotary evaporation
  6. distillationthe product is purified by distillation

Sources & evidence

ORD record
ord-526527637dce46ca951cac3224295f45
Source dataset
uspto-grants-1980_07
Patent number
US04210742

Reaction notes

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