HuagongsheHuagongshe Chemistry Print Report · For research reference only
Fumaric Acid → 5-Trimethylsilyl-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Fumaric Acid | HCID 444972 | — |
| Reactant | 5-(Trimethylsilyl)-3-(1-methyl-2-pyrrolidinyl)pyridine | HCID 19694296 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 5-Trimethylsilyl-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate | HCID 19694303 | 51% |
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 (5 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-trimethylsilyl-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate, (51%). M.p. 161°-162° C. (EtOAc); 1H NMR (D2O, 300 MHz): δ 8.48 (s, 2 H), 8.26 (s, 1 H), 6.25 (s, 3 H), 4.24 (bm, 1 H), 3.53 (bm, 1 H), 3.03 (bm, 1 H), 2.43 (s, 3 H), 2.27 (m, 1 H), 1.9-2.1 (m, 3 H), 0.0 (s, 9 H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05723477 |
| Source dataset | uspto-grants-1998_03 |
| ORD ID | ord-c2497e75ae4e46b1beb5da566107c8e5 |
| Source note | uspto-grants-1998_03 |