Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Amino-2-methyl-1-propanol | HCID 11807 | — |
| Reactant | 3-Hydroxyazetidine hydrochloride | HCID 2759290 | — |
| Reactant | 2-[(3-Iodophenyl)(1-methylpiperidin-4-yloxy)methyl]benzothiazole | HCID 56947458 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Product | Oxalate | HCID 71081 | — |
| Product | 1-{3-[Benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenyl}azetidin-3-ol | HCID 66835885 | — |
Reaction Steps
A screw-capped tube is charged with 2-[(3-iodophenyl)(1-methylpiperidin-4-yloxy)methyl]benzothiazole (example 41, 150 mg), copper(I) iodide (15 mg), deanol (1 mL), potassium carbonate (306 mg), azetidin-3-ol, hydrochloride (88 mg). The tube is evacuated, filled with argon and sealed. After stirring at 60° C. for 100 h, the mixture is diluted with dichloromethane, water and ammonia. After decantation, the aqueous phase is extracted with dichloromethane. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 95/5/0.5 to 90/10/0.5). The base is converted into its oxalate salt in acetone to give 1-{3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenyl}azetidin-3-ol, oxalate melting at 117° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09029357B2 |
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| Source dataset | uspto-grants-2015_05 |
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| ORD ID | ord-6e6c0498cda54f36bcbc663690a7ac65 |
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| Source note | uspto-grants-2015_05 |
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