Triethylamine → 1-Benzyl 2-ethyl piperidine-1,2-dicarboxylate

HRID 421792Notes

Reaction equation

HRID 421792 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(N(CC)CC)C.[CH:19]1[CH:24]=[CH:23][C:22]([CH2:25][O:26][C:27](Cl)=[O:28])=[CH:21][CH:20]=1>CN(C)C1C=CN=CC=1.ClCCl>[N:1]1([C:27]([O:26][CH2:25][C:22]2[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=2)=[O:28])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 27517Ethyl piperidine-2-carboxylate

Product 1

HCID 3592141-Benzyl 2-ethyl piperidine-1,2-dicarboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl piperidine-2-carboxylate (15 g, 95 mmol), triethylamine (27 ml, 191 mmol) and 4-dimethylaminopyridine (0.58 g, 4.8 mmol) in dichloromethane (100 ml) at 0° C. is added a solution of benzyl chloridocarbonate (17 g, 100 mmol) dropwise. The reaction is allowed to warm slowly to room temperature. It is stirred at room temperature overnight (16 h), then allowed to stand for 2 days. The crude product is extracted with dichloromethane, washed with 1 N hydrochloric acid, saturated aqueous sodium bicarbonate solution and brine. The organic phase is dried with anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography over silica gel 60 (300 g) with cyclohexane/ethyl acetate as eluent to afford a pale yellow oil.

Workup

  1. waitto stand for 2 days
  2. extractionThe crude product is extracted with dichloromethane
  3. washwashed with 1 N hydrochloric acid, saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialThe organic phase is dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by flash chromatography over silica gel 60 (300 g) with cyclohexane/ethyl acetate as eluent
  8. customto afford a pale yellow oil

Sources & evidence

ORD record
ord-36f42627df124415841c644b5d76aade
Source dataset
uspto-grants-2012_01
Patent number
US08101615B2

Reaction notes

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