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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 233751Generated: October 27, 2026

Fumaric Acid → 5-(4-Hydroxyphenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate

https://huagongshe.com/reaction/233751

Reaction equation

Participants

RoleNameHCIDCharge
ReactantFumaric AcidHCID 444972—
Reactant4-[5-(1-Methyl-2-pyrrolidinyl)-3-pyridinyl]phenolHCID 19694311—
SolventMethanolHCID 887—
Product5-(4-Hydroxyphenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarateHCID 1969434046%

Reaction Steps

The above-described pyridine derivative was converted into invention compound of Formula I by the addition of one equivalent of fumaric acid to a methanol (15 mL) solution of the free amine at 25° C. After 30 minutes the solvent was removed in vacuo and the residue pumped under high vacuum. Trituration with diethyl ether followed by recrystallization from ethyl acetate afforded 5-(4-hydroxyphenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate, (46%). M.p. 136°-137° C. (EtOAc); 1H NMR (DMSO-d6, 300 MHz): δ 8.76 (s, 1 H), 8.47 (s, 1 H), 8.00 (s, 1 H), 7.58 (d, J=6 Hz, 2 H), 6.90 (d, J=6 Hz, 2 H), 6.62 (s, 2 H), 3.53 (m, 1 H), 3.37 (m, 1 H), 2.55 (m, 1 H), 2.3o (s, 3 H), 1.9 (m, 4 H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05594011
Source datasetuspto-grants-1997_01
ORD IDord-e385eefd21034a809cf6debb82a60514
Source noteuspto-grants-1997_01