HuagongsheHuagongshe Chemistry Print Report · For research reference only
Bromide ion → 1-(3,5-Di-tert-butyl-4-hydroxyphenyl)-2-[(pyridin-2-ylmethyl)amino]ethanone hydrobromide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Bromide ion | HCID 259 | — |
| Reactant | 2-Pyridinemethanamine | HCID 19509 | — |
| Reactant | 2-Bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-one | HCID 616161 | — |
| Reactant | Lithium bis(trimethylsilyl)amide | HCID 57426343 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1-(3,5-Di-tert-butyl-4-hydroxyphenyl)-2-[(pyridin-2-ylmethyl)amino]ethanone hydrobromide | HCID 86632958 | 48.8% |
Reaction Steps
2-(Aminomethyl)pyridine (100 mg) was initially introduced in absolute THF (12 ml) and treated with lithium hexamethyldisilazane solution (1.01 ml, 1 M in THF) at RT with stirring and under argon. After 30 min, 2-bromo-1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethanone (0.5 eq., 151 mg, dissolved in 1.5 ml absolute THF) was added dropwise. For completion of the reaction, the remaining amount of bromide (151 mg) was added and after 2 hours the precipitate formed was filtered off with suction and dried. The 98 mg of the title compound obtained are contaminated with small amounts of THF which, however, do not interfere with the further reaction.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07863269B2 |
| Source dataset | uspto-grants-2011_01 |
| ORD ID | ord-95d0713d57cf489f97dd908458377bb5 |
| Source note | uspto-grants-2011_01 |