HuagongsheHuagongshe Chemistry Print Report · For research reference only
Thionyl Chloride → 1,2,3,6-Tetrahydro-4-phenylpyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | Phosphorus tribromide | HCID 24614 | — |
| Reactant | 2,3,4,9-tetrahydro-1h-carbazol-3-ylmethanol | HCID 282365 | — |
| Reactant | HCID 13491214 | HCID 13491214 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 1,2,3,6-Tetrahydro-4-phenylpyridine | HCID 82553 | — |
| Product | HCID 13326801 | HCID 13326801 | — |
| Product | 3-(Bromomethyl)-2,3,4,9-tetrahydro-1H-carbazole | HCID 13491215 | — |
Reaction Steps
A solution of 2.19 g of 3-chloromethyl-1,2,3,4-tetrahydrocarbazole (or 2.63 g of 3-bromomethyl-1,2,3,4-tetrahydrocarbazole) (obtainable by reduction of 1,2,3,4-tetrahydrocarbazole-3-carboxylic acid with LiAlH4 to give 3-hydroxymethyl-1,2,3,4-tetrahydrocarbazole, followed by reaction with SOCl2 or PBr3) and 1.6 g of 4-phenyl-1,2,3,6-tetrahydropyridine in 10 ml of acetonitrile is stirred at 20° for 12 hours, worked up as usual and 3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)1,2,3,4-tetrahydrocarbazole ("P") is obtained. M.p. 163°-65°.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04698351 |
| Source dataset | uspto-grants-1987_10 |
| ORD ID | ord-39483a14a89c45278cdd80c9de792ab1 |
| Source note | uspto-grants-1987_10 |