2-Bromotoluene → HCID 13041246, compound

HRID 2265134Notes

Reaction equation

C([Li])CCC.CCCCCC.Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].[CH2:20]([N:27]1[CH2:32][CH2:31][C:30](=[O:33])[CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+].C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:20]([N:27]1[CH2:32][CH2:31][C:30]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])([OH:33])[CH2:29][CH2:28]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

Conditions

Temperature: -78 °C

Procedure

In a nitrogen atmosphere, 75 mL of 1.50 M n-butyllithium/hexane solution was dropwise added to tetrahydrofuran (100 mL) solution of 12 mL of 2-bromotoluene at −78° C., and stirred at −78° C. for 30 minutes. Tetrahydrofuran (50 mL) solution of 18.5 mL of 1-benzyl-4-piperidone was dropwise added to the reaction liquid, and stirred at room temperature for 4 hours. Aqueous saturated ammonium chloride solution and aqueous saturated sodium hydrogencarbonate solution were added in that order to the reaction liquid, extracted with ether, and the ether layer was washed with saturated saline water and dried with anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure to obtain crude 1-benzyl-4-o-tolylpiperidin-4-ol as a yellow oily substance.

Workup

stirringstirred at room temperature for 4 hours
extractionextracted with ether
washthe ether layer was washed with saturated saline water
dry with materialdried with anhydrous sodium sulfate
customThe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record: ord-5213b3b79cca482d845d7552845578f9
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855294B2

Reaction notes

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