HCID 68459425, compound → HCID 68458596, compound

HRID 1182414Notes

Reaction equation

HRID 1182414 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].C(C(C)=O)C>[CH:1]([NH:10][C:4]1([CH3:11])[CH2:5][CH2:6][CH2:7][CH:8]([NH:9][CH:6]([CH2:7][CH3:8])[CH3:5])[C:3]1([CH2:1][CH3:2])[CH2:12][CH3:13])([CH2:3][CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 68459425HCID 68459425, compound

Product 1

HCID 68458596HCID 68458596, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
130 °C

Procedure

Diethyl(methyl)-1,3-cyclohexanediamine, as a mixture of its 2,4-diethyl-6-methyl- and 4,6-diethyl-2-methyl-isomers (3.0 g), Pt(S)/C (0.4 g), Amberlyst-15 (0.4 g), and methyl ethyl ketone (45 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 130° C. under 125 psig (9.63×105 Pa) of H2 for 6 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 10° 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′-di-sec-butyl-[diethyl(methyl)-1,3-cyclohexanediamine].

Workup

  1. customThe closed autoclave was purged 3 times with 125 psig (9.63×105 Pa) of H2 at 22° C.
  2. customto remove traces of air
  3. temperatureThe product mixture was cooled to 22° C.
  4. customdegassed
  5. custom100° C.
  6. customfor 5 minutes
  7. customtemperature, 270° C.

Sources & evidence

ORD record
ord-c4aae5e138ce492889862b892deda2bd
Source dataset
uspto-grants-2007_10
Patent number
US07288677B2

Reaction notes

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