Potassium Carbonate → ethyl 2-(4-hydroxypiperidin-1-yl)acetate

HRID 352203Notes

Reaction equation

HRID 352203 reaction equation
Br[CH2:2][CH2:3][O:4][C:5](=[O:7])[CH3:6].C(=O)([O-])[O-].[K+].[K+].[OH:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>O1CCCC1>[CH2:3]([O:4][C:5](=[O:7])[CH2:6][N:18]1[CH2:19][CH2:20][CH:15]([OH:14])[CH2:16][CH2:17]1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 79341Piperidin-4-ol

Product 1

HCID 28837749ethyl 2-(4-hydroxypiperidin-1-yl)acetateYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of bromoethylacetate, 3.3 mL (30.0 mmol) in 100 mL of tetrahydrofuran was added 4.2 g (30.0 mmol) of potassium carbonate and 3.0 mL (30.0 mmol) of 4-hydroxypiperidine. The reaction mixture stirred overnight at rt. and was concentrated to dryness. The residue was partitioned between 20% isopropanol/chloroform and saturated aqueous NaHCO3. The mixture was washed with saturated NaHCO3, washed with brine, dried over Na2SO4, filtered and concentrated to dryness to give 4.65 g (83%) of the desired product as a tan oil. MS (ion spray) 188.0 (M+).

Workup

  1. concentrationand was concentrated to dryness
  2. customThe residue was partitioned between 20% isopropanol/chloroform and saturated aqueous NaHCO3
  3. washThe mixture was washed with saturated NaHCO3
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9a282d30fbb84af982ece30a4188246a
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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