HCID 56635899, compound → HCID 20231523, compound

HRID 28189Notes

Reaction equation

HRID 28189 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].[Al]>[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, compound

Product 1

HCID 20231523HCID 20231523, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 72632029Rhodium aluminiumCatalystHCID 6386tert-ButanolSolvent

Procedure

250 g (1 mol) of 3,12-diisopropyl-1,2-diaza-1,5,9-cyclododecatriene (diastereoisomeric mixture) is dissolved in 1000 ml of t-butanol in an autoclave with stirrer. After the addition of 25 g of a rhodium/aluminium catalyst (5% by weight of rhodium), hydrogen is injected up to a pressure of 130-150 bars, and hydrogenation is then performed at 150°-180° C. until completion of hydrogen absorption. After cooling, the excess hydrogen is released, the suspension is drawn out by suction, and the catalyst is filtered off through a small amount of "Hyflo" (filtering agent). The filtrate is concentrated in a rotary evaporator, and the product is purified by distillation. There is obtained, as the main fraction, 238 g (94% of theory) of 3,12-diamino-2,13-dimethyltetradecane in the form of colourless oil [b.p. 106°-109° C./0.01 Torr; nD20 =1.4600; IR (liquid) inter alia bands at 3355, 3278 and 1613 cm-1 ].

Workup

  1. customis then performed at 150°-180° C. until completion of hydrogen absorption
  2. temperatureAfter cooling
  3. filtrationthe catalyst is filtered off through a small amount of "Hyflo" (filtering agent)
  4. concentrationThe filtrate is concentrated in a rotary evaporator
  5. distillationthe product is purified by distillation

Sources & evidence

ORD record
ord-ed4293050ae34080a0d5aa30ff476024
Source dataset
uspto-grants-1980_09
Patent number
US04225701

Reaction notes

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