Ammonia → 2,2,12-Trimethyltridecane-1,11-diamine
Reaction equation
[CH3:1][C:2]([CH3:19])([CH2:6][CH:7]=[CH:8][CH2:9][CH2:10][CH:11]=[CH:12][CH2:13][CH:14]([CH:16]([CH3:18])[CH3:17])[NH2:15])[CH:3]=[N:4]O.N.[H][H].O>CO.[Ni]>[CH:16]([CH:14]([NH2:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:2]([CH3:1])([CH3:19])[CH2:3][NH2:4])([CH3:18])[CH3:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
490 g (1.84 mols) of 2,2-dimethyl-11-isopropyl-11-amino-undeca-4,8-dienal-oxime is dissolved in 2.4 liters of methanol, and the solution is transferred, together with about 200 g of liquid ammonia, with the addition of 150 g of Raney nickel, to a 6.3-liter steel autoclave. Hydrogen is subsequently injected up to a pressure of 100 bars, and the temperature is raised to 100° C. with stirring. Hydrogenation is performed for about 5 hours under these conditions; the mixture is then cooled, and the ammonia and excess hydrogen are released. Subsequent distillation under high vacuum yields 436 g (1.705 mols) of 1-isopropyl-10,10-dimethyl-1,11-diaminoundecane in the form of colourless liquid clear as water; yield 92.6% of theory; b.p. 87° C./4 Pa; nD20 =1.4619.
Workup
- temperaturethe mixture is then cooled
- distillationSubsequent distillation under high vacuum
Sources & evidence
- ORD record
- ord-a694e7deb8314ce4b5b0edbbdd1adf8a
- Source dataset
- uspto-grants-1984_07
- Patent number
- US04460790
Reaction notes
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