Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Phenethylamine | HCID 1001 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | Tri-tert-butylphosphine tetrafluoroborate | HCID 2734635 | — |
| Reactant | HCID 66835733 | HCID 66835733 | — |
| Catalyst | Molybdenum carbonyl (Mo(CO)6) | HCID 98885 | — |
| Catalyst | trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II) | HCID 11104995 | — |
| Product | HCID 67512215 | HCID 67512215 | — |
Reaction Steps
A screw-capped tube is charged with 2-[(3-bromo-phenyl)(1-methylpiperidin-4-yloxy)methyl]benzothiazole (example 27, 400 mg), N-benzylmethylamine (178 μL), 1,8-diazabicyclo(5.4.0)undec-7-ene (100 μL), trans-di-μ-acetatobis[2-(di-o-tolyl-phosphino)benzyl]dipalladium(II) (22 mg), tri-tert-butylphosphonium tetrafluoroborate (17 mg), molybdenum hexacarbonyl (127 mg) and tetrahydrofurane (3 mL). The tube is sealed and heated at 125° C. for 10 min. The reaction was allowed to cool to room temperature and concentrated under reduced pressure. The residue is purified over silica gel (gradient dichloromethane/methanol/ammonia from 98/2/0.5 to 95/5/0.5) to afford 3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]-N-benzyl-N-methyl-benzamide which is then converted into its oxalate salt in acetone to give 3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]-N-benzyl-N-methylbenzamide, oxalate melting at 103° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08802664B2 |
|---|
| Source dataset | uspto-grants-2014_08 |
|---|
| ORD ID | ord-7f50a2e472704a7ba3f86ad3e033abcb |
|---|
| Source note | uspto-grants-2014_08 |
|---|
