Hydrochloric Acid → 2-Amino-6-(4-aminophenyl)-6-methylheptane

HRID 2296370

Reaction equation

HRID 2296370 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.O[C:11]([CH3:19])([CH3:18])[CH2:12][CH2:13][CH2:14][CH:15]([NH2:17])[CH3:16].[OH-].[Na+]>[Cl-].[Zn+2].[Cl-].[Ta].O>[NH2:17][CH:15]([CH2:14][CH2:13][CH2:12][C:11]([C:6]1[CH:7]=[CH:8][C:3]([NH2:2])=[CH:4][CH:5]=1)([CH3:19])[CH3:18])[CH3:16]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 10969Heptaminol HydrochlorideHCID 14798Sodium Hydroxide

Product 1

HCID 201566692-Amino-6-(4-aminophenyl)-6-methylheptaneYield 82%

Reagents, catalysts & solvents 3

HCID 23956TantalumCatalystHCID 3007855ZincchlorideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
185 °C

Procedure

To a solution of 102 parts of anhydrous zinc chloride in 153 parts of 36% w/w aqueous hydrochloric acid and 200 parts of water are added 140 parts of aniline and 136 parts of 6-hydroxy-6-methyl-2-heptylamine hydrochloride (heptaminol hydrochloride). The whole is charged to a 1 liter tantalum-lined autoclave and stirred at 185° C. for 24 hours. The reaction mixture, after being discharged from the autoclave, is added to a hot solution of 750 parts sodium hydroxide in 1500 parts of water and stirred until cool. The organic phase is extracted with diethylether, washed with water, evaporated and distilled under reduced pressure. After recovering 58 parts of aniline there are obtained 135 parts of 2-amino-6-(4-amino-phenyl)-6-methyl-heptane boiling point 138°-40° C./65 Pa (82% yield based on heptaminol).

Workup

  1. stirringstirred
  2. temperatureuntil cool
  3. extractionThe organic phase is extracted with diethylether
  4. washwashed with water
  5. customevaporated
  6. distillationdistilled under reduced pressure
  7. customAfter recovering 58 parts of aniline

Sources & evidence

ORD record
ord-3e401ff2a45b426fa5a1c001b420fd1b
Source dataset
uspto-grants-1984_01
Patent number
US04429110

Linked notes

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