Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Piperidin-4-ol | HCID 79341 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | HCID 22283149 | HCID 22283149 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86584940 | HCID 86584940 | — |
Reaction Steps
To a suspension of 0.070 g of 4-methoxy-7-(2-methyl-thiazol-4-yl)-benzothiazol-2-ylamine (0.00025 Mol) in THF (4 ml) at room temperature were added 0.054 ml N-ethyl-diisopropylamine (0.00031 Mol) and 0.001 g DMAP. 0.025 g of triphosgen (0.000085 Mol) were added and the whole mixture was heated to 70° C. for 1 hr. Then another 0.054 ml N-ethyl-diisopropylamine (0.00031 Mol) and 0.031 g of 4-hydroxy-piperidin (0.00031 Mol) were added and the reaction mixture was stirred at 70° C. for 1.5 hrs. Upon cooling to room temperature a precipitation formed, which was filtered and washed with THF. The filtrate was evaporated and the residue was subjected to column chromatography (silicagel, CH2Cl2/MeOH 9:1). The title product was obtained as a white solid (11%); F.p.: 145-150° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07317007B2 |
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| Source dataset | uspto-grants-2008_01 |
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| ORD ID | ord-276bb30fbc4c4a0c832d29f1f6262b59 |
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| Source note | uspto-grants-2008_01 |
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