Hydrochloric Acid → 3,5-Dichloro-2-hydroxy-4-[2-(4-methylpiperazin-1-yl)-ethoxy]benzoic acid methyl ester

HRID 2229816Notes

Reaction equation

HRID 2229816 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][OH:10])[CH2:4][CH2:3]1.[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[C:18]([Cl:20])[C:17](O)=[C:16]([Cl:22])[C:15]=1[OH:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>C(Cl)(Cl)Cl>[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[C:18]([Cl:20])[C:17]([O:10][CH2:9][CH2:8][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[C:16]([Cl:22])[C:15]=1[OH:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 2311841-(2-Hydroxyethyl)-4-methylpiperazineHCID 15489807Methyl 3,5-dichloro-2,4-dihydroxybenzoate

Product 1

HCID 538925843,5-Dichloro-2-hydroxy-4-[2-(4-methylpiperazin-1-yl)-ethoxy]benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-(4-methylpiperazin-1-yl)ethanol (14.42 g) and 3,5-dichloro-2,4-dihydroxybenzoic acid methyl ester (52.15 g) in chloroform (400 ml) were added triphenylphosphine (28.85 g) and azodicarboxylic acid diisopropyl (21.7 ml) at room temperature, and the mixture was stirred for 16 hours. 1N Hydrochloric acid (300 ml) was added to the reaction mixture for extraction to give a crude product of the title compound.

Sources & evidence

ORD record
ord-17b4b438abf04868a1b1a9504e8ec164
Source dataset
uspto-grants-2002_07
Patent number
US06420561B1

Reaction notes

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