HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 2-[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-2-methanamine | HCID 11194490 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-[N-(Benzyloxycarbonyl)-N-methylaminomethyl]-1H-indole | HCID 57440843 | 80.6% |
Reaction Steps
N-(Benzyloxycarbonyloxy)succinimide (17.10 g, 68.6 mmole) was added to a solution of 2-(methylaminomethyl)-1H-indole (10.00 g, 62.4 mmole), from Preparation 33, and triethylamine (9.60 mL, 68.6 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 K2CO3 and concentrated. Flash chromatography on silica gel (20% ethyl acetate/hexanes) gave the title compound (14.80 g, 80%) as an off-white solid: MS (ES) m/e 295 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07557125B2 |
| Source dataset | uspto-grants-2009_07 |
| ORD ID | ord-39f21cc0c68d409984362c5a97ab2135 |
| Source note | uspto-grants-2009_07 |