2-Bromoethanol → [1-(2-Hydroxy-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

HRID 2279281Notes

Reaction equation

HRID 2279281 reaction equation
Br[CH2:2][CH2:3][OH:4].[C:5]([O:9][C:10](=[O:18])[NH:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)([CH3:8])([CH3:7])[CH3:6].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:5]([O:9][C:10](=[O:18])[NH:11][CH:12]1[CH2:17][CH2:16][N:15]([CH2:2][CH2:3][OH:4])[CH2:14][CH2:13]1)([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 45076484[1-(2-Hydroxy-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl esterYield 97.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-ethanol (2.38 mL, 33.5 mmol, 1.0 eq) is added at room temperature to a stirred solution of piperidin-4-yl-carbamic acid tert-butyl ester (7.0 g, 33.5 mmol, 1.0 eq) in N,N-dimethylformamide (300 mL), followed by potassium carbonate (4.64 g, 33.5 mmol, 1.0 eq). After 6 hours stirring at room temperature, solvent is evaporated and the residue is extracted with ethyl acetate (3×40 mL) and water (40 mL). pH of the aqueous layer is neutralized with a 0.1 N hydrochloric acid aqueous solution. The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford [1-(2-hydroxy-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester as an off-white oil (7.96 g, 97% yield).

Workup

  1. customsolvent is evaporated
  2. extractionthe residue is extracted with ethyl acetate (3×40 mL) and water (40 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8ff6115a17b449478ebb64cbe9a841bc
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

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