1-Piperidineacetic acid, ethyl ester → Piperidin-1-yl-acetic acid

HRID 64075Notes

Reaction equation

HRID 64075 reaction equation
[N:1]1([CH2:7][C:8]([O:10]CC)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>Cl>[N:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 6434661-Piperidineacetic acid, ethyl ester

Product 1

HCID 201097Piperidin-1-yl-acetic acidYield 60%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The solution of ethyl 2-(piperidin-1-yl)acetate (2.4 g, 14.0 mmol, 1.0 eq) in 8 N HCl was stirred at 95° C. for 16 h. The mixture was concentrated on vacuum pump and quenched and extracted as in Intermediate Example 15(b). The solvent was distilled off to afford the product in 60% yield (1.2 g). LC-MS (ESI): Calculated mass: 143.1; Observed mass 144.4 [M+H]+ (rt: 0.21 min).

Workup

  1. concentrationThe mixture was concentrated on vacuum pump
  2. customquenched
  3. extractionextracted as in Intermediate Example 15(b)
  4. distillationThe solvent was distilled off
  5. customto afford the product in 60% yield (1.2 g)
  6. customObserved mass 144.4 [M+H]+ (rt: 0.21 min)

Sources & evidence

ORD record
ord-fa250c7a410a424eb9b5d41a75fb6808
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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