HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 3-[N-(benzyloxycarbonyl)-N-methylaminomethyl]-1H-indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzyl succinimido carbonate | HCID 83172 | — |
| Reactant | N-Methyl-1H-indole-3-methanamine | HCID 96388 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-[N-(benzyloxycarbonyl)-N-methylaminomethyl]-1H-indole | HCID 22139086 | 74% |
Reaction Steps
N-(Benzyloxycarbonyloxy)succinimide (8.9 g, 35.7 mmole) was added to a solution of 3-(methylaminomethyl)-1H-indole (5.2 g, 32.5 mmole), from Preparation 16, and triethylamine (5.0 mL, 65.7 mmole) in DMF (100 mL) at RT. The reaction was stirred overnight then was concentrated in vacuo. The residue was diluted with water and the mixture was extracted with ethyl acetate. The combined extracts were dried over Na2SO4 and concentrated. Flash chromatography on silica gel (33% ethyl acetate/hexanes) gave the title compound (7.0 g, 74%) as an off-white solid: MS (ES) m/e 295 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07879872B2 |
| Source dataset | uspto-grants-2011_02 |
| ORD ID | ord-38be4b2947004d61a0dbe2298676b65a |
| Source note | uspto-grants-2011_02 |