Piperidin-4-ol → HCID 86629752, compound

HRID 1510234Notes

Reaction equation

HRID 1510234 reaction equation
Br[CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH:14]1[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]1.C(=O)(O)[O-].[Na+]>C(O)C>[OH:20][CH:17]1[CH2:18][CH2:19][N:14]([CH:2]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 79341Piperidin-4-olHCID 97780Ethyl bromophenylacetateHCID 516892Sodium Bicarbonate

Product 1

HCID 86629752HCID 86629752, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl bromo(phenyl)acetate (5.0 g) in ethanol (20 mL) was added 4-piperidinol (5.05 g) and the mixture was stirred at 60° C. for 4 hours. The mixture was poured into dilute sodium bicarbonate aqueous solution and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethylacetate (3:7) to afford ethyl (4-hydroxypiperidin-1-yl)(phenyl)acetate (5.21 g) as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethylacetate (3:7)

Sources & evidence

ORD record
ord-c5415a1bb9d74e3db375d2ef50c79a31
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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