Aniline → HCID 23498320, compound

HRID 1836074Notes

Reaction equation

HRID 1836074 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=O)[CH2:8]2.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl.[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[K+]>O>[NH:12]([CH:2]1[CH:3]2[CH2:9][CH:7]3[CH2:6][CH:5]([CH2:10][C:1]1([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:8]3)[CH2:4]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 8870Benzenamine hydrochloride (1:1)HCID 14797Potassium HydroxideHCID 64151Adamantanone

Product 1

HCID 23498320HCID 23498320, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 13 g of 2-adamantanone, 55 g of aniline, and 15 g of aniline hydrochloride was introduced to a flask with a water remover. The mixture was heated and refluxed at 200° C. (oil bath) under nitrogen atmosphere. Forty hours later, a KOH solution was added so that the pH was approximately 10, and the mixture was extracted with chloroform and washed with water. The mixture was then dried with sodium sulfate, evaporated, and purified with silica gel column chromatography, to obtain 5 g of dianilinoadamantane as a colorless amorphous material.

Workup

  1. temperatureThe mixture was heated
  2. extractionthe mixture was extracted with chloroform
  3. washwashed with water
  4. dry with materialThe mixture was then dried with sodium sulfate
  5. customevaporated
  6. custompurified with silica gel column chromatography

Sources & evidence

ORD record
ord-476585b639934fdbb89e3a2e21e7f854
Source dataset
uspto-grants-2004_08
Patent number
US06777111B1

Reaction notes

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