Benzyl Bromide → Methyl 2-[(phenylmethyl)oxy]-5-(1-piperidinylsulfonyl)benzoate

HRID 1623690Notes

Reaction equation

HRID 1623690 reaction equation
C([O-])([O-])=O.[K+].[K+].[OH:7][C:8]1[CH:17]=[CH:16][C:15]([S:18]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)(=[O:20])=[O:19])=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11].Br[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CC(C)=O>[C:29]1([CH2:28][O:7][C:8]2[CH:17]=[CH:16][C:15]([S:18]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)(=[O:20])=[O:19])=[CH:14][C:9]=2[C:10]([O:12][CH3:13])=[O:11])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 14266920Methyl 2-hydroxy-5-(1-piperidinylsulfonyl)benzoate

Product 1

HCID 67107209Methyl 2-[(phenylmethyl)oxy]-5-(1-piperidinylsulfonyl)benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

K2CO3 (203 mg, 1.47 mmol) was added to a stirred solution of methyl 2-hydroxy-5-(1-piperidinylsulfonyl)benzoate (may be prepared as described in Description 67; 400 mg, 1.34 mmol) in acetone (20 ml), followed by the addition of (bromomethyl)benzene (251 mg, 1.47 mmol). The mixture was heated at reflux for 16 h, and then cooled to room temperature. The mixture was filtered, and the filtrate was concentrated to yield the title compound as a colourless oil. 300 mg.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-59bd5940383f46a6900231dc2e39de68
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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