Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | HCID 178479251 | HCID 178479251 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178474961 | HCID 178474961 | 61.2% |
Reaction Steps
To a stirred mixture of Trans-4-[2-(4-Benzo[1,3]dioxol-4-yl-piperidin-1-yl)-ethyl]-cyclohexylamine hydrochloride (intermediate A) (50 mg, 0.136 mmol) in DMF (0.8 ml) was added N,N-diisopropylethylamine (62 mg, 0.0833 ml, 0.477 mmol), acetic acid (9.82 mg, 9.35 μl, 0.164 mmol) and TBTU (52.4 mg, 0.164 mmol). The mixture was allowed to stir at room temperature for 4 h and poured into ice/water (0.5 ml) The crude reaction mixture was concentrated in vacuo. The reaction mixture was solved with sat NaHCO3 (1×10 mL). and extracted with dichloromethane (3×20 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 10 g, 0% to 20% MeOH in dichloromethane) to yield the title compound as an white solid (31 mg, 61%), MS (ISP) m/z=373.5 [(M+H)+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08598357B2 |
|---|
| Source dataset | uspto-grants-2013_12 |
|---|
| ORD ID | ord-db0705dc3b4244ec9a5d750fd97f161a |
|---|
| Source note | uspto-grants-2013_12 |
|---|