4-(1-Aminoethyl)phenol → 1,2-Bis[1-methyl-1-(4-hydroxyphenyl)ethylamino]ethane

HRID 1905548Notes

Reaction equation

HRID 1905548 reaction equation
[NH2:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[NH2:12][CH:13]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[CH3:14].N[CH:23](C1C=CC=CC=1O)[CH3:24].N[C:33](C1C=CC=CC=1O)(C)C.C(NC(C1C=CC(O)=CC=1)(C)C)CCC.OCCNC(C1C=CC(O)=CC=1)(C)C.CN(C(C1C=CC(O)=CC=1)C)N.CC(NNC(C1C=CC(O)=CC=1)(C)C)(C1C=CC(O)=CC=1)C.CC(NO)(C1C=CC(O)=CC=1)C.CC(C1C=CC(O)=CC=1)=C>>[CH3:3][C:2]([NH:1][CH2:23][CH2:24][NH:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)([CH3:33])[CH3:14])([C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=1)[CH3:4]

Participants

11

Reactant 10

HCID 1235944-(1-Aminoethyl)phenolHCID 2414562-(1-Aminoethyl)phenolHCID 584247p-IsopropenylphenolHCID 141781264-(2-Aminopropan-2-yl)phenolHCID 200358172-(Butylamino)-2-(4-hydroxyphenyl)propaneHCID 200358181-Methyl-1-(4-hydroxyphenyl)ethylhydrazineHCID 20035820N-[1-methyl-1-(4-hydroxyphenyl)ethyl]hydroxylamineHCID 200358222-(2-Aminopropan-2-yl)phenolHCID 20035824N,N'-bis[1-methyl-1-(4-hydroxyphenyl)ethyl]hydrazineHCID 200358252-(2-Hydroxyethylamino)-2-(4-hydroxyphenyl)propane

Product 1

HCID 200358231,2-Bis[1-methyl-1-(4-hydroxyphenyl)ethylamino]ethane

Procedure

Novel α-aminoalkylphenols are produced by the process described hereinabove. Examples of typical α-aminoalkylphenols include 2-amino-2-(4-hydroxyphenyl)-propane, 1-amino-1-(4-hydroxyphenyl)ethane, 1-amino-1-(2-hydroxyphenyl)ethane, 2-amino-2-(2-hydroxyphenyl)-propane, 2-(butylamino)-2-(4-hydroxyphenyl)propane, 2-(2-hydroxyethylamino)-2-(4-hydroxyphenyl)propane, 1-methyl-1-(4-hydroxyphenyl)ethylhydrazine, N,N'-bis[1-methyl-1-(4-hydroxyphenyl)ethyl]hydrazine, and N-[1-methyl-1-(4-hydroxyphenyl)ethyl]hydroxylamine. When polyamines such as 1,2-aminoethane are employed as the amine, bis(α-aminoalkylphenol)s can be produced by employing the proper stoichiometry. For example, 2 moles of 1-(1-methylethenyl)-4-hydroxybenzene can react with 1 mole of 1,2-aminoethane to form 1,2-bis[1-methyl-1-(4-hydroxyphenyl)ethylamino]ethane. Preferred α-aminoalkylphenols are represented generally by the formula: ##STR2## whereom R. Ra, Rb and Rc are as previously defined. Preferably, R, Ra, Rb and Rc are independently H or lower alkyl. Most preferably, Rb is methyl; R, Ra, and Rc are H; and the hydroxy moiety is para to the alkylamino moiety.

Workup

  1. customcan be produced

Sources & evidence

ORD record
ord-3a86e8e94f1147f7bd52e48e197c7d9e
Source dataset
uspto-grants-1989_06
Patent number
US04843160

Reaction notes

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