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

HRID 233751Notes

Reaction equation

HRID 233751 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:14]3[CH2:18][CH2:17][CH2:16][N:15]3[CH3:19])[CH:11]=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[C:20]([OH:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24]>CO>[C:20]([OH:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24].[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:14]3[CH2:18][CH2:17][CH2:16][N:15]3[CH3:19])[CH:11]=[N:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 196943114-[5-(1-Methyl-2-pyrrolidinyl)-3-pyridinyl]phenol

Product 1

HCID 196943405-(4-Hydroxyphenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarateYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  1. customAfter 30 minutes the solvent was removed in vacuo
  2. customTrituration with diethyl ether followed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-e385eefd21034a809cf6debb82a60514
Source dataset
uspto-grants-1997_01
Patent number
US05594011

Reaction notes

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