Water → HCID 67259319, compound

HRID 84308Notes

Reaction equation

HRID 84308 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[NH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][OH:16])[CH2:11][CH2:10]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>CN(C)CCO.[Cu]I>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][OH:16])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 115221-Bromo-4-iodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 4207714-Piperidinemethanol

Product 1

HCID 67259319HCID 67259319, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 79022-(Dimethylamino)ethanolSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 1-bromo-4-iodo-benzene (2.5 g, 8.8 mmol), piperidine-4-yl-methanol (2.0 g, 17.7 mmol), potassium phosphate (3.8 g, 17.7 mmol) and copper (I) iodide (3.8 g, 17.7 mmol) in N,N-dimethyl ethanolamine (8.4 mL) was heated to 55° C. for 48 hours. The mixture was allowed to cool to ambient temperature, water was added and the mixture was extracted with ether 2×. The combined organic extracts were washed with water 3×. The organic extract was dried over magnesium sulfate, filtered and concentrated to a crude residue. The residue was dissolved in methylene chloride and passed through a silica gel pad. The pad was eluted ethyl acetate/heptanes (3:7) to ethyl acetate/heptanes (6:4) and the filtrate was concentrated in vacuo to afford [1-(4-bromo-phenyl)-piperidin-4-yl]-methanol as a white solid. (2.4 g)

Workup

  1. temperatureto cool to ambient temperature
  2. extractionthe mixture was extracted with ether 2×
  3. washThe combined organic extracts were washed with water 3×
  4. extractionThe organic extract
  5. dry with materialwas dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a crude residue
  8. dissolutionThe residue was dissolved in methylene chloride
  9. washThe pad was eluted ethyl acetate/heptanes (3:7) to ethyl acetate/heptanes (6:4)
  10. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-375ac0fc473a4812b054a345472bfe58
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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