Methacrylic Acid → Dimethylamine

HRID 1954491Notes

Reaction equation

C[C:2]([N:14](C)[CH3:15])(CO)C[C:4]1[CH:5]=[CH:6][C:7]([Cl:11])=[C:8]([Cl:10])[CH:9]=1.[C:17]([OH:22])(=[O:21])[C:18]([CH3:20])=[CH2:19].[Cl:23]C1C=C(C=CC=1Cl)N>>[Cl:23][C:18]([CH3:20])([CH2:19][C:4]1[CH:5]=[CH:6][C:7]([Cl:11])=[C:8]([Cl:10])[CH:9]=1)[C:17]([OH:22])=[O:21].[CH3:2][NH:14][CH3:15]

Participants

Reactant 3

HCID 4093Methacrylic Acid

HCID 72573,4-Dichloroaniline

HCID 131074Cericlamine

Product 2

HCID 674Dimethylamine

HCID 10978444HCID 10978444, compound

Procedure

Process for the preparation of cericlamine which consists: i) in arylating methacrylic acid with the diazonium chloride of 3,4-dichloroaniline, to obtain (+/-)2-chloro-3-(3,4-dichlorophenyl)-2-methylpropionic acid, ii) in aminating the acid with dimethylamine, to obtain (+/-)3-(3,4-dichlorophenyl)-2-dimethylamino-2-methylpropionic acid, or an alkaline metal salt thereof, iii) in esterifying the amino-acid or its salt, then, iv) in reducing the ester by a metal or organometal hydride to obtain (+/-)3-(3,4-dichlorophenyl)-2-dimethylamino-2-methyl-propan-1-ol.

Sources & evidence

ORD record: ord-fbb009953aa54c14b2bfe09e13554fe7
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06121491

Reaction notes

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