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

HRID 1929216Notes

Reaction equation

HRID 1929216 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:22][CH2:23][OH:24]>C(O)C>[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:22][CH2:23][OH:24])[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 108982-BromoethanolHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 45076484[1-(2-Hydroxy-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl esterYield 165.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Piperidin-4-yl-carbamic acid tert-butyl ester (5 g, 25 mmol) is dissolved in 100 ml of ethanol. After addition of sodium carbonate (10.6 g, 100 mmol), 2-bromo-ethanol (3.55 ml, 50 mmol) is added dropwise. The reaction mixture is refluxed for 16 h and then evaporated. The residue is dissolved in 100 ml of dichloromethane and filtrated. The residue is washed with DCM. The combined filtrates are evaporated, which afforded 10.1 g of a yellow oil, which is further purified by flash chromatography (silicagel, DCM/methanol/conc. ammonia 90:9:1).

Workup

  1. additionis added dropwise
  2. temperatureThe reaction mixture is refluxed for 16 h
  3. customevaporated
  4. dissolutionThe residue is dissolved in 100 ml of dichloromethane
  5. filtrationfiltrated
  6. washThe residue is washed with DCM
  7. customThe combined filtrates are evaporated

Sources & evidence

ORD record
ord-d9825c7006594db087c0dc785b8d4acd
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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