Benzyl chloroformate → Benzyl 3-acetylpiperidine-1-carboxylate

HRID 1013558Notes

Reaction equation

HRID 1013558 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7](=[O:9])[CH3:8])[CH2:2]1.CCN(C(C)C)C(C)C.[CH:19]1[CH:24]=[CH:23][C:22]([CH2:25][O:26][C:27](Cl)=[O:28])=[CH:21][CH:20]=1>C(Cl)Cl>[C:7]([CH:3]1[CH2:4][CH2:5][CH2:6][N:1]([C:27]([O:26][CH2:25][C:22]2[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=2)=[O:28])[CH2:2]1)(=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 219094881-(Piperidin-3-yl)ethan-1-one

Product 1

HCID 53249939Benzyl 3-acetylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(piperidin-3-yl)ethanone (53, 2.6 g, 20 mmol) in DCM (100 ml) at room temperature was added DIEA (5.2 ml, 30 mmol). A solution of Cbz-Cl (4.4 ml, 30 mmol) in DCM (20 ml) was added dropwise over 2 hrs. The mixture was stirred at room temperature for 17 hrs, washed with water, saturated sodium bicarbonate (aq.), water, 1N HCl (aq.) and brine, dried over anhydrous sodium sulfate. The drying agent was removed by filtration. The filtrate was concentrated under vacuum to give the benzyl 3-acetylpiperidine-1-carboxylate (54) which was used in the next step without further purification. LC-MS for C15H19NO3 calcd: 261; found: 262.

Workup

  1. washwashed with water, saturated sodium bicarbonate (aq.), water, 1N HCl (aq.) and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe drying agent was removed by filtration
  4. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-56088956e3b349dbb8f2ff9c64bfdaa7
Source dataset
uspto-grants-2011_07
Patent number
US07981925B2

Reaction notes

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