HuagongsheHuagongshe Chemistry Print Report · For research reference only
Fumaric Acid → 5-(4-Hydroxyphenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Fumaric Acid | HCID 444972 | — |
| Reactant | 4-[5-(1-Methyl-2-pyrrolidinyl)-3-pyridinyl]phenol | HCID 19694311 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 5-(4-Hydroxyphenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate | HCID 19694340 | 46% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05594011 |
| Source dataset | uspto-grants-1997_01 |
| ORD ID | ord-e385eefd21034a809cf6debb82a60514 |
| Source note | uspto-grants-1997_01 |