Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Cyanobenzoic acid | HCID 15875 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1-(4-Chlorobenzyl)-4-[(valylamino)methyl]piperidine | HCID 53782731 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 54167831 | HCID 54167831 | — |
Reaction Steps
A solution of 1-(4-chlorobenzyl)-4-{(valylamino)methyl}piperidine (20 mg, 0.059 mmol) in CH2Cl2 (0.60 mL) was treated with Et3N (0.011 mL, 0.077 mmol), m-cyanobenzoic acid (28 mg, 0.071 mmol), EDCI (13 mg, 0.065 mmol) and HOBt (9 mg, 0.065 mmol). The reaction mixture was stirred at 25° C. for 16 h. The resulting solution was diluted with CH2Cl2 (0.75 mL), washed with 2 N aqueous NaOH solution (2×0.75 mL) and dried by filtration through a PTFE membrane. Concentration afforded the 1-(4-chlorobenzyl)-4-[{N-(3-cyanobenzoyl)valyl}aminomethyl]piperidine (compound No. 619) (24.2 mg, 88%) which required no further purification: The purity was determined by RPLC/MS (85%); ESI/MS m/e 467 (M++H, C26H31ClN4O2).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06410566B1 |
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| Source dataset | uspto-grants-2002_06 |
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| ORD ID | ord-64b180eaba164a9aa1e3ce743dd7539a |
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| Source note | uspto-grants-2002_06 |
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