HuagongsheHuagongshe Chemistry Print Report · For research reference only
N-(2-Aminoethyl)piperidine → 2-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (2-piperidine-1-yl-ethyl)-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N-(2-Aminoethyl)piperidine | HCID 33944 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | 2-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid | HCID 24966534 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (2-piperidine-1-yl-ethyl)-amide | HCID 24967257 | 22% |
Reaction Steps
To solution of 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (70.2 mg, 0.17 mmol) and 2-piperidine-1-yl-ethylamine (0.049 ml, 0.35 mmol) in DMF 5.0 mL was added HBTU (132.7 mg, 0.35 mmol) and DIPEA (0.061 ml, 0.35 mmol). After stirring at room temperature, the mixture was partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4 anh), and concentrated. The residue was purified by silica gel column chromatography (CH2Cl2:MeOH=20:1) to give 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (2-piperidine-1-yl-ethyl)-amide as a white foam (18.9 mg, 22% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08394799B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-993be1a0ba1d45218f215f987aaa69c3 |
| Source note | uspto-grants-2013_03 |