Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | HCID 19784344 | HCID 19784344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 53643503 | HCID 53643503 | 59% |
Reaction Steps
0.34 g (3 mmol) of methanesulfonyl chloride dissolved in tetrahydrofuran was added dropwise at 0° C. to 1.0 g (3 mmol) of the product from Example 3 and 0.6 g (6 mmol) of triethylamine in 100 ml of anhydrous tetrahydrofuran. The mixture was stirred at room temperature for 16 h and then the solvent was removed under reduced pressure. The residue was partitioned between aqueous sodium bicarbonate solution and methylene chloride, and the organic phase was dried and concentrated under reduced pressure. The resulting oil was purified by chromatography (eluent: methylene chloride/methanol 10:1). 0.73 g of 1-(4-cyanophenyl)-4-(2-(4-methanesulfonylaminophenyl)-N-methylethylamino) piperidine was obtained. 1H NMR (d -DMSO) δ=1.3-1.5 (2H); 1.7 (2H); 2.1 (3H); 2.5-2.7 (4H); 2.7-3.0 (5H); 3.3 (1H); 3.9 (2H); 6.9 (2H); 7.0-7.2 (4H); 7.5 (2H) and 9.6 (1H) ppm.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05260318 |
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| Source dataset | uspto-grants-1993_11 |
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| ORD ID | ord-b18f579367534f5ea533d57d99f262ad |
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| Source note | uspto-grants-1993_11 |
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