HuagongsheHuagongshe Chemistry Print Report · For research reference only
Piperidine → 1-(5-Cyano-2-pyridinyl)-4-piperidinecarboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-Chloroethyl chloroformate | HCID 521305 | — |
| Reactant | 4-{(3S,4S)-3-(4-Chloro-phenyl)-4-[(S)-1-(3,4-dichloro-phenoxy)-ethyl]-piperidine-1-carbonyl}-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carbonitrile | HCID 46870889 | — |
| Reactant | (R)-1-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanol | HCID 59438191 | — |
| Reactant | HCID 178516119 | HCID 178516119 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 1-(5-Cyano-2-pyridinyl)-4-piperidinecarboxylic acid | HCID 16227474 | — |
| Product | 4-{(3s,4s)-3-(4-Chloro-phenyl)-4-[(s)-1-(5-fluoro-pyridin-2-yloxy)-ethyl]-piperidine-1-carbonyl}-3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-5'-carbonitrile | HCID 46870977 | — |
Reaction Steps
In analogy to the procedure described for the synthesis of 4-{(3S,4S)-3-(4-Chloro-phenyl)-4-[(S)-1-(3,4-dichloro-phenoxy)-ethyl]-piperidine-1-carbonyl}-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carbonitrile (example 49) the respective piperidine derivative was prepared from (R)-1-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanol and 5-fluoro-2-hydroxy pyridine via Mitsunobu reaction and subsequently the benzyl group was cleaved by treatment with 1-chloroethyl-chloroformate, DIPEA and methanol. Coupling with 5′-Cyano-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid (commercially available) yielded the title compound as viscous yellow oil. MS (m/e): 548.4 [(M+H)+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08324248B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-639561d283aa4da9a140d5add2a75d1b |
| Source note | uspto-grants-2012_12 |