Potassium Carbonate → Tert-butyl 4-(4-hydroxy-4-phenylpiperidin-1-yl)benzoate

HRID 2085805Notes

Reaction equation

HRID 2085805 reaction equation
[OH:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:14]([O:18][C:19](=[O:27])[C:20]1[CH:25]=[CH:24][C:23](F)=[CH:22][CH:21]=1)([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)C>[OH:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][N:5]([C:23]2[CH:24]=[CH:25][C:20]([C:19]([O:18][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:27])=[CH:21][CH:22]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 963874-Phenylpiperidin-4-olHCID 2736444Tert-butyl 4-fluorobenzoate

Product 1

HCID 22730002Tert-butyl 4-(4-hydroxy-4-phenylpiperidin-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
125 °C

Procedure

A solution of 4-hydroxy-4-phenyl piperidine (221 mg, 1.25 mmol) in DMSO (1 mL) was treated with tert-butyl-4-fluorobenzoate (196 mg, 1.00 mmol) and powdered potassium carbonate (173 mg, 1.25 mmol), stirred vigorously at 125° C. for 16 hours, cooled to room temperature, diluted with diethyl ether, washed with brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS (DCI(+)) m/e 354 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0c15f43e97534ffc8a2c67d83920b228
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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