Ethyl chloroacetate → 1-Piperidineacetic acid, ethyl ester

HRID 64069

Reaction equation

HRID 64069 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>CN(C=O)C>[N:1]1([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 8082PiperidineHCID 11430Potassium Carbonate

Product 1

HCID 6434661-Piperidineacetic acid, ethyl esterYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of piperidine (3.4 g, 40.7 mmol, 1.0 eq) in DMF were added K2CO3 (14 g, 101.0 mmol, 2.5 eq.) and ethyl 2-chloroacetate (4.83 ml, 48.9 mmol, 1.2 eq). The mixture was stirred at RT for 16 h. The mixture was quenched and extracted as in Intermediate Example 5(a). The solvent was distilled off to give the product in 72% yield (5 g). LC-MS (ESI): Calculated mass: 171.1; Observed mass 172.3 [M+H]+ (rt: 0.1 min).

Workup

  1. customThe mixture was quenched
  2. extractionextracted as in Intermediate Example 5(a)
  3. distillationThe solvent was distilled off
  4. customto give the product in 72% yield (5 g)
  5. customObserved mass 172.3 [M+H]+ (rt: 0.1 min)

Sources & evidence

ORD record
ord-4d5b8ba09a57434995d6e8df42992feb
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Linked notes

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