HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 4-[4-(4-Methanesulfonyl-phenoxymethyl)-thiazol-2-yl]-piperazine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-(Methylsulfonyl)phenol | HCID 123350 | — |
| Reactant | Tert-butyl 4-[4-(chloromethyl)-1,3-thiazol-2-YL]piperazine-1-carboxylate | HCID 18186678 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | 4-[4-(4-Methanesulfonyl-phenoxymethyl)-thiazol-2-yl]-piperazine-1-carboxylic acid tert-butyl ester | HCID 25026514 | — |
Reaction Steps
A mixture of 4-(4-Chloromethyl-thiazol-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (700 m g, 2.20 mmol), 4-methanesulfonyl-phenol (417 mg, 1.1 eq.) and K2CO3 (609 mg, 2 eq.) in acetone (30 mL) was heated to reflux overnight. After cooling, the solid was filtered off through a pad of celite. The filtrate was concentrated in vacuo. The crude product was purified on silica gel (EtOAc:hexanes=1:1) to afford the desired product as an off-white solid. 1H NMR (CDCl3): δ 7.87 (2H, d, J=8.8 Hz), 7.12 (2H, d, J=8.8 Hz), 6.59 (1H, s), 5.05 (2H, s), 3.56 (4H, m), 3.48 (4H, m), 3.04 (3H, s), 1.49 (9H, s).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08975258B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-e6d4925f381a42b6a5d534f89109832b |
| Source note | uspto-grants-2015_03 |