Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Cyclohexanol | HCID 7966 | — |
| Reactant | Tolylboronic acid | HCID 79799 | — |
| Reactant | HCID 11234753 | HCID 11234753 | — |
| Reactant | HCID 86621020 | HCID 86621020 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 68855817 | HCID 68855817 | — |
Reaction Steps
In an analogous manner to Example 135, step 3, 1-[1-(4′-methyl-1,1′-biphenyl-4-yl)-2-(4-methylpiperazin-1-yl)ethylcyclohexanol dihydrochloride was prepared from 1-(4-bromophenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclohexanol (see Example 180, step 3) using 4-tolylboronic acid. Salt formation: A solution of 1-[1-(4′-methyl-1,1′-biphenyl-4-yl)-2-(4-methylpiperazin-1-yl)ethyl]cyclohexanol, in diethyl ether (2 mL) was treated with a 4 N solution of hydrogen chloride in dioxane (1 mL) and stored in the refrigerator for 16 h. The resulting crystals were collected, washed with diethyl ether, and dried in vacuo to yield 1-[1-(4′-methyl-1,1′-biphenyl-4-yl)-2-(4-methylpiperazin-1-yl)ethyl]cyclohexanol dihydrochloride. MS (ESI) m/z 393 ([M+H]+); HRMS: calcd for C26H36N2O.2.00 HCl, 464.2361; found (ESI), 393.2913.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07550456B2 |
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| Source dataset | uspto-grants-2009_06 |
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| ORD ID | ord-a5711f9409cf43d595fc6bba6e2aba9d |
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| Source note | uspto-grants-2009_06 |
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