Acetonitrile → HCID 57507753, compound

HRID 2074288Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C.[OH:19][C:20]1[CH:25]=[CH:24][C:23]([S:26][CH:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]2)=[CH:22][CH:21]=1>[Cl-].[Na+].O>[F:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26][CH:27]2[CH2:28][CH2:29][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31][CH2:32]2)=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1-(Bromomethyl)-3-fluorobenzene (0.436 ml) and potassium carbonate (670 mg) were added to an acetonitrile (15 ml) solution containing tert-butyl 4-[(4-hydroxyphenyl)sulfanyl]piperidine-1-carboxylate (1.00 g), followed by heating at 80° C. for 2 hours. The reaction solution was cooled, saturated brine was added thereto, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane:EtOAc=8:1 (v/v)) to obtain tert-butyl 4-({4-[(3-fluorobenzyl)oxy]phenyl}sulfanyl)piperidine-1-carboxylate (1.50 g) as colorless powder.

Workup

temperatureThe reaction solution was cooled
extractionfollowed by extraction with chloroform
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customthe resulting residue was purified by silica gel column chromatography (eluent: hexane:EtOAc=8:1 (v/v))

Sources & evidence

ORD record: ord-5cb85ab4c190414e93a4d4e3af8b3cde
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919495B2

Reaction notes

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