Water → HCID 20459474, compound

HRID 544124Notes

Reaction equation

HRID 544124 reaction equation
[CH3:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH:4]=[N:5][CH2:6][CH2:7][N:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][NH:8][CH2:7][CH2:6][NH:5][CH2:4][C:3]1[CH:17]=[CH:18][CH:19]=[CH:20][C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 20459481HCID 20459481, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20459474HCID 20459474, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5.3 g of N,N'-di-(o-methylbenzylidene)-ethylenediamine, dissolved in 75 ml of tetrahydrofuran, are added dropwise to a suspension of 2.0 g of lithium aluminium hydride in 30 ml of tetrahydrofuran. The mixture is heated under reflux for 30 minutes, the excess of reducing agent is decomposed with water while cooling with ice, the whole is poured into 200 ml of sodium hydroxide solution (10% by weight) and extracted 3 times by shaking with 150 ml of diethyl ether each time. From the combined diethyl ether extracts the hydrochloride is precipitated, in form of a white powder, by adding a solution of hydrogen chloride in diethyl ether. The hydrochloride is separated by filtration, shaken with 150 ml of diethyl ether and 150 ml of 10% sodium hydroxide solution. The ether phase is dried over magnesium sulphate and concentrated to dryness by evaporation. The residue is recrystallised from ethyl acetate. N,N'-di-(o-methylbenzyl)-ethylenediamine having a meltinp point of 38°-39° C. is obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 30 minutes
  3. temperaturewhile cooling with ice
  4. extractionextracted 3 times
  5. customis precipitated, in form of a white powder
  6. additionby adding a solution of hydrogen chloride in diethyl ether
  7. customThe hydrochloride is separated by filtration
  8. stirringshaken with 150 ml of diethyl ether and 150 ml of 10% sodium hydroxide solution
  9. dry with materialThe ether phase is dried over magnesium sulphate
  10. concentrationconcentrated to dryness by evaporation
  11. customThe residue is recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-2589eb8d55be46288e44ca8a0816dde0
Source dataset
uspto-grants-1984_05
Patent number
US04448776

Reaction notes

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