Potassium Carbonate → 4-(2-Formyl-4-iodo-phenoxymethyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1095066Notes

Reaction equation

HRID 1095066 reaction equation
[I:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([CH2:30]Br)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>CN(C)C=O.C(OCC)(=O)C>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([CH2:30][O:10][C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:9][C:6]=2[CH:7]=[O:8])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2526125-IodosalicylaldehydeHCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate

Product 1

HCID 577431634-(2-Formyl-4-iodo-phenoxymethyl)-piperidine-1-carboxylic acid tert-butyl esterYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-iodosalicylaldehyde (2 g, 8.2 mmol) (Aldrich) in N,N-dimethylformamide (20 mL) was added anhydrous K2CO3 (1.15 g, 8.2 mmol), and 4-bromomethyl-piperidine -1-carboxylic acid tert-butyl ester (2.3 g, 8.2 mmol, Pharmacore). The reaction mixture was heated at 60° C. for 18 h. The crude was cooled to room temperature, diluted with ethyl acetate, washed with water, brine. The organic layer was separated, dried over MgSO4, concentrated to give 4-(2-formyl-4-iodo-phenoxymethyl)-piperidine-1-carboxylic acid tert-butyl ester (Yield 2.3 g, 63%).

Workup

  1. temperatureThe crude was cooled to room temperature
  2. washwashed with water, brine
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-af5f65185357411ead3f1547b498ad26
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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