Potassium Carbonate → HCID 59331944, compound

HRID 1798385Notes

Reaction equation

HRID 1798385 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:21]2[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=2)([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:29][CH2:30][O:31][CH3:32].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([C:21]2[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=2)([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:29][CH2:30][O:31][CH3:32])=[CH:16][CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 809722-Bromoethyl methyl etherHCID 59331934HCID 59331934, compound

Product 1

HCID 59331944HCID 59331944, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(4-Bromo-phenyl)-4-(4-hydroxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (100 mg, 0.23 mmol), 2-bromoethyl methylether (200 ul) and potassium carbonate (64 mg, 0.46 mmol) in dimethylformamide (2 ml) was heated in a CEM Explorer™ microwave to 50° C. for 30 minutes using 50 watts power. The reaction was poured into sodium hydroxide (2N, 4 ml), stirred for 5 minutes then extracted into ethyl acetate (2×30 ml). The combined organic liquors were dried (MgSO4), concentrated and the residue was purified by column chromatography (SiO2), eluting with ethyl acetate/petrol (25:75) gradient to (50:50) to afford the title compound (82 mg). LCMS: (PS-A2) Rt 4.00 [M+H]+490.

Workup

  1. extractionthen extracted into ethyl acetate (2×30 ml)
  2. dry with materialThe combined organic liquors were dried (MgSO4)
  3. concentrationconcentrated
  4. customthe residue was purified by column chromatography (SiO2)
  5. washeluting with ethyl acetate/petrol (25:75) gradient to (50:50)

Sources & evidence

ORD record
ord-c18acd0bd5cf481fbbaf64e43c0cc4ee
Source dataset
uspto-grants-2013_01
Patent number
US08343953B2

Reaction notes

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