Ammonia → 2,2,12-Trimethyltridecane-1,11-diamine

HRID 2164688Notes

Reaction equation

[NH3:1].[CH3:2][C:3]1([CH3:18])[CH2:14][CH:13]=[CH:12][CH2:11][CH2:10][CH:9]=[CH:8][CH2:7][CH:6]([CH:15]([CH3:17])[CH3:16])[N:5]=[CH:4]1.[H][H]>[Ni].[OH-].[Na+]>[CH:15]([CH:6]([NH2:1])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:3]([CH3:18])([CH3:2])[CH2:4][NH2:5])([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 175 °C

Procedure

75 g of a 25% aqueous ammonia solution are placed together with 10 g of Raney nickel and 20 ml of 1N aqueous NaOH as well as 52.2 g (0.2 mol) of 3,3-dimethyl-12- isopropyl-1-aza-1,5,9-cyclododecatriene into an autoclave with magnetic stirrer. After the reaction mixture has been heated to 175° C., hydrogen gas is injected up to a total pressure of 50 bar. After a reaction time of 9 hours, the mixture is cooled and distilled. There is obtained 65% of the theoretical yield of 1-isopropyl-10,10-dimethyl-1,11-diaminoundecane.

Workup

temperatureAfter a reaction time of 9 hours, the mixture is cooled
distillationdistilled

Sources & evidence

ORD record: ord-04095f1b8be34b428e858a38774dc18f
Source dataset: uspto-grants-1985_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04506099

Reaction notes

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