HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonium Chloride → Tert-butyl 4-{2-[3-(aminocarbonyl)phenyl]ethyl}-1-piperidinecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 3-{2-[1-(Tert-butoxycarbonyl)-4-piperidinyl]ethyl]benzoic acid | HCID 57421826 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Tert-butyl 4-{2-[3-(aminocarbonyl)phenyl]ethyl}-1-piperidinecarboxylate | HCID 57421827 | 60.9% |
Reaction Steps
3-{2-[1-(Tert-butoxycarbonyl)-4-piperidinyl]ethyl}benzoic acid (17.8 g) was dissolved in DMF (200 ml), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (15.4 g) and 1-hydroxybenzotriazole (10.8 g) were added thereto, followed by stirring at room temperature for 2 hours. Ammonium chloride (8.57 g) and TEA (22.3 ml) were added to the reaction liquid, followed by stirring overnight at room temperature. An aqueous saturated sodium hydrogencarbonate solution was added to the reaction liquid, and the precipitated crystal was collected by filtration and dried to obtain tert-butyl 4-{2-[3-(aminocarbonyl)phenyl]ethyl}-1-piperidinecarboxylate (10.8 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07919495B2 |
| Source dataset | uspto-grants-2011_04 |
| ORD ID | ord-5ee10ee441974b25a35db9a5fbc55643 |
| Source note | uspto-grants-2011_04 |