Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | (Benzyloxy)acetic acid | HCID 290301 | — |
| Reactant | 1-Benzyl-4-piperidylamine | HCID 415852 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 69313663 | HCID 69313663 | 69.4% |
Reaction Steps
2.00 g (12.0 mmol) of benzyloxyacetic acid was dissolved in 40 mL of dichloromethane and 2.77 g (14.4 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 2.21 g (14.4 mmol) of 1-hydroxybenzotriazole 1 hydrate, 2.52 mL (18.1 mmol) of triethylamine and 2.52 g (13.2 mmol) of 4-amino-1-benzylpiperidine were added thereto under ice-cooling, followed by stirring of the mixture at room temperature for 18 hours. Dichloromethane was added to the reaction mixture and the mixture was washed successively with a saturated aqueous sodium hydrogencarbonate solution, water and a saturated NaCl solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel chromatography (eluting solvent: ethyl acetate/methanol=100/0-90/10) to obtain 2.82 g (yield: 69%) of the title compound as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07365067B2 |
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| Source dataset | uspto-grants-2008_04 |
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| ORD ID | ord-57391fc912c243c5bad8e9fd3f3d42ac |
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| Source note | uspto-grants-2008_04 |
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