HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → (4-benzyl-4-hydroxy-piperidin-1-yl)-(2-methyl-1H-indol-3-yl)-methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 4-Benzyl-4-piperidinol | HCID 98152 | — |
| Reactant | 2-Methyl-1H-indole-3-carboxylic acid | HCID 3159671 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (4-benzyl-4-hydroxy-piperidin-1-yl)-(2-methyl-1H-indol-3-yl)-methanone | HCID 66744648 | 75.5% |
Reaction Steps
To a stirred solution of 0.1 g (0.57 mmol) 2-methyl-1H-indole-3-carboxylic acid in 10 ml CH2Cl2 were added 0.14 g (0.73 mmol) EDC, 0.10 g (0.73 mmol) HOBt, 90 μl (0.63 mmol) Et3N and 0.11 g (0.57 mmol) 4-benzyl-piperidin-4-ol. The mixture was stirred overnight at RT and then poured onto water and extracted with CH2Cl2. The combined organic phases were dried over Na2SO4 and concentrated in vacuo. Flash chromatography (ethyl acetate) afforded 0.15 g (75%) of (4-benzyl-4-hydroxy-piperidin-1-yl)-(2-methyl-1H-indol-3-yl)-methanone as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07781436B2 |
| Source dataset | uspto-grants-2010_08 |
| ORD ID | ord-e7e7ad9f0321405daf5b9b9351055ffb |
| Source note | uspto-grants-2010_08 |