Potassium Iodide → HCID 20512406, compound

HRID 1164451Notes

Reaction equation

HRID 1164451 reaction equation
[Cl:1][CH:2]([CH3:15])[CH2:3][NH:4][C:5]1[C:10]([CH2:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:13][CH3:14].[CH2:16]([C:18]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][CH3:26])[C:19]=1[NH2:20])[CH3:17].[I-].[K+]>C(O)(C)C>[ClH:1].[ClH:1].[CH2:13]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][CH3:12])[C:5]=1[NH:4][CH2:3][CH:2]([NH:20][C:19]1[C:21]([CH2:25][CH3:26])=[CH:22][CH:23]=[CH:24][C:18]=1[CH2:16][CH3:17])[CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 113692,6-DiethylanilineHCID 20512421HCID 20512421, compound

Product 1

HCID 20512406HCID 20512406, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 46.3 g (0.205 moles) of N-(β-chloropropyl)-2,6-diethyl-aniline, obtained as indicated in point (b) above, 61.2 g (0.41 moles) of 2,6-diethylaniline and 1.66 g (10 mmoles) of potassium iodide is stirred at 140° to 145° C. for 4 hours under nitrogen atmosphere. The mixture is allowed to cool, 150 ml of isopropanol are added, and the resulting mixture is stirred at 0° to +5° C. for 2 hours. The separated 2,6-diethylaniline hydrochloride (19.2 g, 25.2%) is filtered off, washed with cold isopropanol and dried. The filtrate is acidified with isopropanolic hydrochloric acid (acid content: about 15 g/100 ml), the separated precipitate is filtered off, washed with cold isopropanol and dried. The resulting crude substance, weighing 72 g, is recrystallized from methanol to obtain 29.4 g (34.8%) of 1,2-bis(2',6'-diethylphenyl-amino)-propane dihydrochloride as a uniform substance; m.p.: 161°-167° C. The base is liberated from this salt as described in point (c) of Example 16 and isolated from the reaction mixture by extraction with chloroform.

Workup

  1. customobtained
  2. temperatureto cool
  3. stirringthe resulting mixture is stirred at 0° to +5° C. for 2 hours
  4. filtrationThe separated 2,6-diethylaniline hydrochloride (19.2 g, 25.2%) is filtered off
  5. washwashed with cold isopropanol
  6. customdried
  7. filtrationthe separated precipitate is filtered off
  8. washwashed with cold isopropanol
  9. customdried
  10. customis recrystallized from methanol

Sources & evidence

ORD record
ord-a919e780df934907a9a8fd3e716a6e93
Source dataset
uspto-grants-1983_01
Patent number
US04369325

Reaction notes

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