Diethyl Ether → N-Ethyl-N',N'-dimethyl-cyclohexane-1,2-diamine

HRID 1701374Notes

Reaction equation

HRID 1701374 reaction equation
[CH3:1][N:2]([C@@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]1[NH:10][C:11](=O)[CH3:12])[CH3:3].CCOCC.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>O>[CH3:1][N:2]([CH3:3])[CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[NH:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 14798Sodium HydroxideHCID 11735567trans-N-[2-(N,N-dimethylamino)cyclohexyl]acetamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 23349800N-Ethyl-N',N'-dimethyl-cyclohexane-1,2-diamineYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of the trans-N-[2-(N,N-dimethylamino)cyclohexyl]acetamide (acetyl compound) (5.03 g.; 0.027 mole) in 100 ml. of ether was added during 10 minutes to a solution of LAH (5.03 g.) in 300 ml. of ether and the mixture was refluxed 24 hours. It was cooled, decomposed in succession with 5 ml. of H2O, 5 ml. of 15% NaOH, and 15 ml. of H2O. The suspension was stirred 1 hour at room temperature, filtered and the cake washed with ether. The solvent was evaporated through a 9" Vigreux and the product distilled at 91° (13 mm), 3.5 g. (76% yield). ir NH3680w, 3,300; CH 2960, 2920, 2850, 2820; N-alkyl 2780, CH/CN 1455, 1265, 1140, 1060, 1045, 1025, 1025. NMR in CDCl3 (100 MHz) was in accord. Mass spectrum M+ 170.

Workup

  1. temperatureIt was cooled
  2. filtrationfiltered
  3. washthe cake washed with ether
  4. customThe solvent was evaporated through a 9" Vigreux
  5. distillationthe product distilled at 91° (13 mm), 3.5 g

Sources & evidence

ORD record
ord-6def271542304c389760948970277000
Source dataset
uspto-grants-1980_03
Patent number
US04192885

Reaction notes

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