Phosgene → HCID 10899720, compound
Reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[NH:3]1.[C:11](Cl)([Cl:13])=[O:12]>C1(C)C(C)=CC=CC=1>[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[N:3]1[C:11]([Cl:13])=[O:12]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 29.7 g (0.21 mol) of redistilled 2,2,6,6-tetramethylpiperidine in 50 ml of xylene is added dropwise in the course of 1.5 hours, at -40°, to 40.2 g of a 25.7% solution of phosgene in xylene (0.105 mol), with stirring and under an inert gas atmosphere. After adding the amine, the mixture is stirred for a further 4 hours at -10° and for 18 hours at -5° to 0°. The 2,2,6,6-tetramethylpiperidinocarboxylic acid chloride which is thus obtained is not isolated but is now treated with a solution of 19.73 g (0.05 mol) of N,N'-bis-(2,2,6,6-tetramethyl-piperid-4-yl)-hexamethylenediamine and 20.4 ml (0.12 mol) of diisopropyl-ethylamine in 50 ml of xylene, this solution being added in the course of 2 hours, at -10°. After stirring for a further 18 hours at room temperature and for 6 hours at 50° C., the reaction mixture is cooled to room temperature, diluted with 300 ml of hexane and extracted four times with 150 ml of water, the organic phase is dried over sodium sulfate and the solvents are distilled off completely under a waterpump vacuum. The residue, which solidifies as crystals after a short time, is recrystallised from acetonitrile, and by this means pure N,N'-bis(2,2,6,6-tetramethylpiperid-4-yl)-N,N'-bis-(2,2,6,6-tetramethylpiperidinocarbonyl)-hexamethylenediamine is obtained as a colourless compound with a melting point of 137°-139°. ##STR40##
Workup
- stirringthe mixture is stirred for a further 4 hours at -10° and for 18 hours at -5° to 0°
Sources & evidence
- ORD record
- ord-48268803c6fa4fd28b1389b370e570da
- Source dataset
- uspto-grants-1983_10
- Patent number
- US04412021
Reaction notes
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