HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → N-Boc 4-{[(2-bromo-4-cyanophenyl)acetyl]amino}piperidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-Amino-1-Boc-piperidine | HCID 1268291 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 2-(3-Bromo-4-cyanophenyl)acetic acid | HCID 66524944 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N-Boc 4-{[(2-bromo-4-cyanophenyl)acetyl]amino}piperidine | HCID 59444100 | 40.6% |
Reaction Steps
A mixture of 3-bromo-4-cyanophenylacetic acid (D134, 2.1 g, 7.00 mmol), 1-Boc 4-aminopiperidine (1.5 g, 7.49 mmol), EDC hydrochloride (1.5 g, 7.82 mmol), diisopropylethylamine (3.0 mL, 17.22 mmol), and DMF (25 mL) was stirred for 2 h at room temperature then diluted with ethyl acetate and washed with aqueous citric acid, aqueous sodium bicarbonate, water, and brine. Crystallisation from diethyl ether gave N-Boc 4-{[(2-bromo-4-cyanophenyl)acetyl]amino}piperidine (1.5 g, 2.84 mmol, 40.6% yield) as a white solid containing about 20% of N-Boc 4-{[(4-cyanophenyl)acetyl]amino}piperidine.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08278328B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-e49f81a0bca94498a067dad1adcbea92 |
| Source note | uspto-grants-2012_10 |