Diethyl Ether → N,N,N'-Trimethyl-cyclohexane-1,2-diamine

HRID 262266Notes

Reaction equation

HRID 262266 reaction equation
[CH3:1][N:2]([CH3:11])[CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1(N)[NH2:9].[CH3:12]COCC.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>O>[CH3:1][N:2]([CH3:11])[CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[NH:9][CH3:12]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 540440342-(Dimethylamino)cyclohexanediamine

Product 1

HCID 13544013N,N,N'-Trimethyl-cyclohexane-1,2-diamineYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of the N-formyl-N-[2-(dimethylamino)-cyclohexanediamine (4 g.; 0.0235 mole) in 50 ml. of ether was added during 5 minutes to a solution of LAH (4 g.) in 250 ml. of ether and refluxed 17 hours. It was cooled in ice, and decomposed in succession with 4 ml. of H2O, 4 ml. of 15% NaOH, 12 ml. of H2O, stirred 1 hour at room temperature and filtered. The cake was washed with ether, and the ether was distilled. The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g. (82% yield). ir NH 3680 v.w., 3320; CH 2940, 2820; N-alkyl 2780; CH 1475, 1450; C-N/other 1270, 1155, 1145, 1125, 1060, 1045, 1005, 870, 805, 775. nmr in CDCl3 (60 MHz) was in accord. Mass spectrum M+ 156.

Workup

  1. temperatureIt was cooled in ice
  2. filtrationfiltered
  3. washThe cake was washed with ether
  4. distillationthe ether was distilled
  5. distillationThe titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g

Sources & evidence

ORD record
ord-45661932b5304457b12cffef16bbe69b
Source dataset
uspto-grants-1979_05
Patent number
US04153717

Reaction notes

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