Sodium Sulfate → 4-(2-Aminopropyl)-3-chloro-N,N-dimethylaniline--hydrogen chloride (1/2)

HRID 1973278Notes

Reaction equation

HRID 1973278 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[C:10]([N+:12]([O-])=O)[CH3:11])=[C:5]([Cl:15])[CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.CCOCC>[ClH:15].[ClH:15].[Cl:15][C:5]1[CH:4]=[C:3]([N:2]([CH3:16])[CH3:1])[CH:8]=[CH:7][C:6]=1[CH2:9][CH:10]([NH2:12])[CH3:11]

Participants

6

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 536498323-Chloro-N,N-dimethyl-4-(2-nitroprop-1-en-1-yl)aniline

Product 1

HCID 30436094-(2-Aminopropyl)-3-chloro-N,N-dimethylaniline--hydrogen chloride (1/2)Yield 170.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 12.0 g of N,N-dimethyl-3-chloro-4-(2-nitropropenyl)aniline in 150 ml of dry tetrahydrofuran is added dropwise with stirring to 8.0 g of lithium aluminum hydride in 200 ml of dry ether. After the addition the reaction mixture is refluxed for 5 hours. 40 ml of saturated sodium sulphate solution is added by portions and the mixture is filtered. The filtrate is dried with anhydrous sodium sulphate and acidified with hydrogen chloride in ether. The precipitate is removed by filtration and recrystallized from ethanol-isopropyl ether. Yield: 9.3 g, m.p. 187°-191°. A second recrystallization from the same solvent yields 8.1 g of the pure compound, melting at 193°-195°.

Workup

  1. additionAfter the addition the reaction mixture
  2. temperatureis refluxed for 5 hours
  3. filtrationthe mixture is filtered
  4. dry with materialThe filtrate is dried with anhydrous sodium sulphate
  5. customThe precipitate is removed by filtration
  6. customrecrystallized from ethanol-isopropyl ether
  7. customA second recrystallization from the same solvent

Sources & evidence

ORD record
ord-a172686491e54655bdb62890102555ab
Source dataset
uspto-grants-1976_12
Patent number
US03996381

Reaction notes

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