HCID 20512421, compound → HCID 20512461, compound

HRID 894596Notes

Reaction equation

HRID 894596 reaction equation
Cl[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]>C(Cl)(Cl)Cl>[CH2:13]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][CH3:12])[C:5]=1[N:4]1[CH2:3][CH:2]([CH3:15])[N:4]([C:5]2[C:6]([CH2:13][CH3:14])=[CH:7][CH:8]=[CH:9][C:10]=2[CH2:11][CH3:12])[CH2:3]1)[CH3:14]

Participants

3

Reactant 1

HCID 20512421HCID 20512421, compound

Product 1

HCID 20512461HCID 20512461, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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 atmoshere. 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-diethyleniline 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.

Sources & evidence

ORD record
ord-051e72361f784dd99c64f8a9b02e74f4
Source dataset
uspto-grants-1981_08
Patent number
US04284642

Reaction notes

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