HCID 20231523, compound → 6,15-Diamino-5,16-diethyleicosane

HRID 2057440Notes

Reaction equation

HRID 2057440 reaction equation
NC(CCCCCCCCC(N)C(C)C)C(C)C.[CH3:19][CH2:20][CH:21]([CH:26]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH:29]([CH:38]([CH2:41][CH2:42][CH2:43][CH3:44])[CH2:39][CH3:40])[NH:28][NH:27]1)[CH2:22][CH2:23][CH2:24][CH3:25]>>[NH2:27][CH:26]([CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH:29]([NH2:28])[CH:38]([CH2:39][CH3:40])[CH2:41][CH2:42][CH2:43][CH3:44])[CH:21]([CH2:20][CH3:19])[CH2:22][CH2:23][CH2:24][CH3:25]

Participants

3

Reactant 2

HCID 20231523HCID 20231523, compoundHCID 23455925HCID 23455925, compound

Product 1

HCID 205590276,15-Diamino-5,16-diethyleicosane

Procedure

The procedure described in (a) is repeated, starting from 74.8 g (0.2 mole) of 3,12-di-(3-heptyl)-1,2-diazacyclododecane (diastereoisomer mixture) and using correspondingly reduced amounts of catalyst and solvent, affording after purification by chromatography and distillation 29.9 g (40% of theory) of 6,15-diamino-5,16-diethyleicosane as a colourless oil [b.p. 170° C./0.01 torr; nD20 =1.4662; IR spectrum (liquid) includes bands at 3278, 1613 cm-1 ]. The 1,2-diaza-1,5,9-cyclododecatrienes and 1,2-diazacyclododecanes used as starting materials can be prepared by the methods described in German Offenlegungsschrift Nos. 2,330,087 and 2,549,403.

Workup

  1. customaffording
  2. customafter purification
  3. distillationby chromatography and distillation 29.9 g (40% of theory) of 6,15-diamino-5,16-diethyleicosane as a colourless oil [b.p. 170° C./0.01 torr
  4. customcan be prepared by the methods

Sources & evidence

ORD record
ord-5987ffeef41144119e2e91be0d1ce45c
Source dataset
uspto-grants-1980_07
Patent number
US04210742

Reaction notes

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