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

HRID 724895

Reaction equation

HRID 724895 reaction equation
[Cl: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].[Cl: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 196943015-(4-Chlorophenyl)-3-(1-methyl-2-pyrrolidinyl) pyridine

Product 1

HCID 196943005-(4-Chlorophenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarateYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above-referenced pyridine 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-chlorophenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate, (72%) as a colorless solid. M.p. 159°-160° C. (EtOAc); 1H NMR (DMSO-d6, 300 MHz): δ 8.84 (d, J=3 Hz, 1H), 8.58 (d, J=3 Hz, 1H), 8.08 (t, J=2 Hz, 1H), 7.79 (d, J=8 Hz, 2H), 7.56 (d, J=8 Hz, 2H), 6.62 (s, 2H), 3.49 (t, J=6 Hz, 1H), 3.32 (m, 1H), 2.52 (m, 1H), 2.28 (m, 1H), 2.24 (s, 3H), 1.9 (m, 3H).

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-39b59cad1d1b4cd49097964658f95288
Source dataset
uspto-grants-1998_01
Patent number
US05705512

Linked notes

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