N-Ethylaniline → HCID 584205, compound

HRID 1091002Notes

Reaction equation

HRID 1091002 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([N:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7670N-EthylanilineHCID 10340Sodium CarbonateHCID 123681,6-Dibromohexane

Product 1

HCID 584205HCID 584205, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

50.8 g of N-ethyl aniline together with 48.8 g of 1,6-dibromohexane and 25.2 g of sodium carbonate were dissolved in 500 ml of toluene. The mixture was stirred while refluxed at 115° C. Reflux was continued overnight. The precipitate was filtered and stirred in 1.25 l of ethyl acetate. The ethyl acetate phase was washed with 500 ml of water and 20 ml of acetic acid. The filtrate and the ethyl acetate phase were washed with a saturated sodium chloride solution and dried on sodium sulfate. The reaction product was isolated by concentration under reduced pressure. 45.4 g of N,N'-diethyl-N,N'-diphenyl-1,6-diaminohexane were obtained (yield: 70%).

Workup

  1. temperatureReflux
  2. filtrationThe precipitate was filtered
  3. stirringstirred in 1.25 l of ethyl acetate
  4. washThe ethyl acetate phase was washed with 500 ml of water and 20 ml of acetic acid
  5. washThe filtrate and the ethyl acetate phase were washed with a saturated sodium chloride solution
  6. customdried on sodium sulfate
  7. customThe reaction product was isolated by concentration under reduced pressure

Sources & evidence

ORD record
ord-252ab3570dff485183d30716668d7abc
Source dataset
uspto-grants-1992_01
Patent number
US05084435

Reaction notes

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