Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1-Butanol | HCID 263 | — |
| Reactant | 4-Methoxybenzylamine | HCID 75452 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-Chloro-3-(fluoromethyl)pyridine | HCID 23160370 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Product | HCID 62735098 | HCID 62735098 | 34% |
Reaction Steps
A mixture of commercially available 2-chloro-3-fluoromethylpyridine (10.53 g, 80 mmol), 4-methoxybenzylamine (12.5 mL, 96 mmol), DIPEA (16.5 mL, 96 mmol) and DMAP (150 mg) in n-butanol (20 mL) was refluxed (oil bath temp. 140° C.) for 12 days. Concentrated in vacuum and directly subjected to chromatography. Silica gel column chromatography gave the title compound as a yellow liquid (6.3 g, 34%). MS (ISP) 233.1 [(M+H)+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08063048B2 |
|---|
| Source dataset | uspto-grants-2011_11 |
|---|
| ORD ID | ord-15506444cec94fa48924bf77f9c5c074 |
|---|
| Source note | uspto-grants-2011_11 |
|---|
