N,N-Dimethyl-1,3-propanediamine → N~1~,N~1~-Dimethyl-N~3~-(2,2,6,6-tetramethylpiperidin-4-yl)propane-1,3-diamine

HRID 1625531Notes

Reaction equation

[CH3:1][C:2]1([CH3:11])[CH2:7][C:6](=O)[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3]1.[CH3:12][N:13]([CH3:18])[CH2:14][CH2:15][CH2:16][NH2:17]>O>[CH3:12][N:13]([CH3:18])[CH2:14][CH2:15][CH2:16][NH:17][CH:6]1[CH2:7][C:2]([CH3:11])([CH3:1])[NH:3][C:4]([CH3:10])([CH3:9])[CH2:5]1

Participants

Conditions

Temperature: 60 °C

Procedure

1808.9 g (11.65 mol) of 2,2,6,6-tetramethyl-4-piperidinone and 1191.1 g (11.66 mol) of N1,N1-dimethyl-1,3-propanediamine are combined in a 4 l reactor and stirred for 2 hours at 60° C. Then, the reaction water is distilled off in vacuum. Thereafter the reaction solution is transferred to an autoclave and admixed with 76 g of Raney nickel. The autoclave is flushed 3 times with 5 bar nitrogen each time. Then, the hydrogenation is carried out by repeated pressurization with 50 bar hydrogen, wherein the reaction mixture is stirred vigorously during the entire reaction time. Then, the reaction mixture is separated by fractional distillation. The product has a boiling point of 130° C. at 4.5 mbar. 2062 g of product could be isolated having a purity of 98.6% and a yield of 72% of theory.

Workup

distillationis distilled off in vacuum
customThe autoclave is flushed 3 times with 5 bar nitrogen each time
stirringis stirred vigorously during the entire reaction time
customThen, the reaction mixture is separated by fractional distillation

Sources & evidence

ORD record: ord-544f9d4ac7964d7cb7e8bc37a672ef96
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08784537B2

Reaction notes

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