Triethylamine → Benzyl ethyl piperidine-1,3-dicarboxylate

HRID 1469125Notes

Reaction equation

HRID 1469125 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13]1.C(N(CC)CC)C>C(Cl)Cl>[N:12]1([C:2]([O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:3])[CH2:17][CH2:16][CH2:15][CH:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 98969Ethyl nipecotate

Product 1

HCID 17999271Benzyl ethyl piperidine-1,3-dicarboxylateYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl chloroformate (Aldrich, cat #:119938) (191 mL, 1.34 mol) was slowly added to a cooled (at 0° C.) mixture of ethyl piperidine-3-carboxylate (Aldrich, cat #:194360) (200 g, 1.27 mol) and triethylamine (266 mL, 1.91 mol) in methylene chloride (1000 mL). The reaction mixture was allowed to gradually warm to ambient temperature and stirred for 3 h. The reaction was quenched by the addition of 1N HCl aq. solution and the product was extracted several times with methylene chloride. The combined extracts were washed with water, saturated aq. NaHCO3, water, brine, dried over MgSO4, filtered and concentrated under reduced pressure to afford the desired product as oil (359.8 g, 97%). LC/MS 292.2 (M+H)+.

Workup

  1. temperaturea cooled
  2. customThe reaction was quenched by the addition of 1N HCl aq. solution
  3. extractionthe product was extracted several times with methylene chloride
  4. washThe combined extracts were washed with water, saturated aq. NaHCO3, water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b90d67065b1c43f8bb7f3f4bc7585306
Source dataset
uspto-grants-2015_04
Patent number
US09006260B2

Reaction notes

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