HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Iodide → N-Methylaniline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1,2,3,4-Tetrahydroquinoline | HCID 69460 | — |
| Reactant | Benzenamine, N-3-butenyl-N-methyl- | HCID 577490 | — |
| Reactant | Ethanol, 1-bromo- | HCID 14202443 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | N-Methylaniline | HCID 7515 | — |
| Product | Homoallyl bromide | HCID 21241 | — |
| Product | Benzenamine, N-3-butenyl-N-methyl- | HCID 577490 | — |
| Product | 1-Phenylpiperidin-4-ol | HCID 2737154 | — |
Reaction Steps
Referring to the above reaction diagram, tetrahydroquinoline may be alkylated in methanol by adding excess bromoethanol, sodium iodide and potassium carbonate and refluxing the solution for 24 hours. The product is preferably isolated in water and purified by vacuum distillation. If phenylpiperazine is the starting material, it is alkylated under the same reaction conditions. A 1-phenyl-4-piperidinol structure is synthesized by preparing N-but-3-enyl--N-methylaniline, and treating with aqueous trifluoroacetic acid. N-but-3-enyl--N-methylaniline is provided by alkylation of N-methylaniline with 4-bromobut-1-ene. 1-Phenyl-3-pyrrolidinol is synthesized by the reaction of aniline with 1,4-dibromo-2-butanol.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05041509 |
| Source dataset | uspto-grants-1991_08 |
| ORD ID | ord-debd344a8a76421cbf09db4f3ee3f141 |
| Source note | uspto-grants-1991_08 |