Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | HCID 23502703 | HCID 23502703 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 23502756 | HCID 23502756 | — |
Reaction Steps
150 mg (0.39 mmol) of [3-(2,6-difluorophenyl)propyl]-[1-(2,6-dimethylphenyl)-2-piperidin-1-ylethyl]amine (corresponds to Example 35) is placed in 3 ml of THF. Then 0.07 ml of DIPEA and 0.02 ml (0.39 mmol) of acetic acid are added; and finally 124.6 mg (0.39 mmol) of TBTU are added. The mixture is then stirred for 6 hours at room temperature, the solvent is eliminated, ethyl acetate and saturated NaHCO3 solution are added, and the resulting mixture is stirred for 15 minutes. The phases are separated and the organic phase is washed twice more with NaHCO3 solution and twice with saturated NaCl solution. The organic phase is dried and evaporated down and the residue is purified by flash chromatography (cyclohexane/ethyl acetate 7:3). MS: m/z 429 [(M+H)+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06770636B2 |
|---|
| Source dataset | uspto-grants-2004_08 |
|---|
| ORD ID | ord-6f7543cc8a2d4e6ba87453881a3a508d |
|---|
| Source note | uspto-grants-2004_08 |
|---|