Hydrochloric Acid → 2-(2,4-Dichlorophenyl)hexyl amine

HRID 1613253Notes

Reaction equation

HRID 1613253 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([CH:11]([C:20]#[N:21])[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])[CH2:8][CH2:9][CH3:10].[Cl-].[NH4+].Cl>CCOCC>[Cl:19][C:13]1[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=1[CH:11]([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:20][NH2:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 123432572-(2,4-Dichlorophenyl)hexane nitrileHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 197756212-(2,4-Dichlorophenyl)hexyl amineYield 108.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 9.0 g (0.24 mole) of lithium aluminum hydride in 200 ml of anhydrous ether is added 57 g (0.24 m) of α-n-butyl-2,4-dichlorobenzyl cyanide dropwise at 10°. The reaction mixture is stirred at room temperature for 30 minutes and at 35° overnight. Excess lithium aluminum hydride is then decomposed by addition of saturated ammonium chloride solution (50 ml), followed by 20% hydrochloric acid (300 ml) at 0°. The acidic aqueous layer is separated and extracted with ether. The combined ether portions are washed with water and dried over MgSO4. When ether is evaporated under vacuo, there is obtained 63 g of a yellow solid. The solid is then dissolved in 20% sodium hydroxide solution and extracted with ether. The combined ether extracts are dried over MgSO4. Solvent is evaporated to give 48 g of an oil. Vacuum distillation (101°-104°/0.1 mm) gives 38.3 g of pure product.

Workup

  1. customThe acidic aqueous layer is separated
  2. extractionextracted with ether
  3. washThe combined ether portions are washed with water
  4. dry with materialdried over MgSO4
  5. customWhen ether is evaporated under vacuo

Sources & evidence

ORD record
ord-4833987a2eb24d47a3cfa583fc705597
Source dataset
uspto-grants-1993_03
Patent number
US05192783

Reaction notes

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