HCID 68459425, compound → HCID 68457287, compound
Reaction equation
[CH2:1]([C:3]1([CH2:12][CH3:13])[CH:8]([NH2:9])[CH2:7][CH2:6][CH2:5][C:4]1([CH3:11])[NH2:10])[CH3:2]>[Pt].CC(C)=O>[CH:1]([NH:10][C:4]1([CH3:11])[CH2:5][CH2:6][CH2:7][CH:8]([NH:9][CH:4]([CH3:11])[CH3:5])[C:3]1([CH2:1][CH3:2])[CH2:12][CH3:13])([CH3:3])[CH3:2]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
Diethyl(methyl)-1,3-cyclohexanediamine, as a mixture of its 2,4-diethyl-6-methyl- and 4,6-diethyl-2-methyl-isomers was made as described in Example 4. Diethyl(methyl)-1,3-cyclohexanediamine, as a mixture of its 2,4-diethyl-6-methyl- and 4,6-diethyl-2-methyl-isomers (10 g), Pt(S)/C (0.5 g), Amberlyst-15 (0.5 g), and acetone (50 g) were charged into a 100 mL metal autoclave at 22° C. The closed autoclave was purged 3 times with 125 psig (9.63×105 Pa) of H2 at 22° C. to remove traces of air. The reaction mixture was then heated at 110-130° C. under 125 psig (9.63×105 Pa) of H2 for 8 hrs (until no further H2 uptake was observed). The product mixture was cooled to 22° C. and degassed. A diluted product sample was analyzed by GC (100° C. for 5 minutes at 110° C. per minute rate; final temperature, 270° C.). The GC data (normalization method) showed 100% conversion of diethyl(methyl)-1,3-cyclohexanediamine, and a 95-97% yield of N,N′-diisopropyl-[diethyl(methyl)-1,3-cyclohexanediamine].
Workup
- customThe closed autoclave was purged 3 times with 125 psig (9.63×105 Pa) of H2 at 22° C.
- customto remove traces of air
- temperatureThe product mixture was cooled to 22° C.
- customdegassed
- custom100° C.
- customfor 5 minutes
- customtemperature, 270° C.
Sources & evidence
- ORD record
- ord-aedc41450df64005b28b4624c6254da4
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07288677B2
Reaction notes
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