Triethylamine → Benzyl 2-(2-hydroxyethyl)piperidine-1-carboxylate

HRID 1857641Notes

Reaction equation

HRID 1857641 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][OH:9].C(N(CC)CC)C.Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>C(OCC)(=O)C>[CH2:21]([O:20][C:18]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][OH:9])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 151442-Piperidin-2-ylethanol

Product 1

HCID 45358666Benzyl 2-(2-hydroxyethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-piperidin-2-yl-ethanol (2.04 g in 50 mL methylene chloride) at 0° C. was added 2.64 mL of triethylamine and 5 mg N,N-dimethylaminopyridine. To the stirred solution, 2.45 mL of benzyl chloroformate was added dropwise and the reaction allowed to proceed at room temperature. After 2 hours, the mixture was diluted with ethyl acetate and washed sequentially with 10% aqueous sodium bisulfate, water and brine. The organic portion was dried over magnesium sulfate and purified by flash chromatography on silica gel (hexane:ethyl acetate, 70:30) to give the title compound (2.05 g).

Workup

  1. customto proceed at room temperature
  2. washwashed sequentially with 10% aqueous sodium bisulfate, water and brine
  3. dry with materialThe organic portion was dried over magnesium sulfate
  4. custompurified by flash chromatography on silica gel (hexane:ethyl acetate, 70:30)

Sources & evidence

ORD record
ord-245a6517c48247d6b44c5ad5eeb8346b
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

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