Potassium Carbonate → 4-(4-Chloro-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester

HRID 504464Notes

Reaction equation

HRID 504464 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].C([O-])([O-])=O.[K+].[K+].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27](OS(C)(=O)=O)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([O:10][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=2[CH:7]=[O:8])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Product 1

HCID 577501934-(4-Chloro-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl esterYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 5-chloro-2-hydroxy-benzaldehyde (3.15 g, 20 mmol), KI (0.1 g) and K2CO3 (8.28 g, 60 mmol) in DMF (100 mL) was added 4-methanesulfonyloxy-piperidine-1-caboxylic acid tert-butyl ester (7.26 g, 26 mmol). The mixture was heated at 100° C. for 2 h, then cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was washed with 1N NaOH (30 mL), water, and dried over anhydrous Na2SO4, concentrated to give the title compound as white solid (Yield: 5.3 g, 78%).

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with 1N NaOH (30 mL), water
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-161b2d1793d5411798675f7de360f4de
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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