HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → 1-(1-Methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl 4-piperidinecarboxylate | HCID 70770 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1-Methylcyclopropanecarboxylic acid | HCID 81326 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-(1-Methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acid ethyl ester | HCID 59438144 | 92% |
Reaction Steps
To a stirred solution of 14.4 g (0.144 mol) 1-methyl-cyclopropanecarboxylic acid in 200 mL DCM was added 27.1 g (0.141 mol) EDC, 19.10 g (0.141 g) HOBt and 35.93 mL (0.259 mol) Et3N. After 1 h at room temperature 18.9 g (0.12 mol) piperidine-4-carboxylic acid ethyl ester was added and the mixture was stirred at room temperature over night. The mixture was poured onto water and extracted with DCM. The combined organic phases were dried over Na2SO4 and concentrated under vacuum. Column chromatography (SiO2, EtOAc/H, 1:1) yielded 26.1 g (92%) of the title compound as a light yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08324248B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-22c4336baba541adbeb8d3556cf60fc3 |
| Source note | uspto-grants-2012_12 |