Dimethylamine → HCID 21418608, compound

HRID 1731067Notes

Reaction equation

HRID 1731067 reaction equation
[CH3:1][NH:2][CH3:3].O=[C:5]1[CH2:12][C:9]([CH3:11])([CH3:10])[CH2:8][C:7]([CH3:13])=[CH:6]1.C(O)C.[H][H]>[Pd].O>[CH3:1][N:2]([CH:5]1[CH2:12][C:9]([CH3:11])([CH3:10])[CH2:8][CH:7]([CH3:13])[CH2:6]1)[CH3:3]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 702EthanolHCID 6544IsophoroneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 21418608HCID 21418608, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 15.8g of dimethylamine, 32g of isophorone, 2g of 5% Palladium on charcoal and 150cc of ethanol was placed in an autoclave. Hydrogen gas was added to increase the pressure to 500 psi. The reaction mixture was heated to 95° C. and kept with stirring at 95° C. for 1 hr. Hydrogen gas was added during the reaction, to maintain a pressure of 330-500 psi. After the mixture was allowed to cool to ambient temperature, the solvent and the water produced were removed under diminished pressure. Distillation yielded 35g of N,N-dimethyl-3,5,5-trimethylcyclohexylamine; b760 196°-198° C; nuclear magnetic resonance spectrum, δ in ppm, 2.18 s, 6H; 2.15-1.00 m's, 8H; 1.17 s, 3H; 0.90 s and 0.88 d, 6H.

Workup

  1. temperatureto increase the pressure to 500 psi
  2. temperatureto maintain a pressure of 330-500 psi
  3. temperatureto cool to ambient temperature
  4. customwere removed under diminished pressure
  5. distillationDistillation

Sources & evidence

ORD record
ord-7fd2d78d15294181879529958f904fc4
Source dataset
uspto-grants-1976_11
Patent number
US03994975

Reaction notes

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