Acetic Acid → HCID 86724914, compound

HRID 714526Notes

Reaction equation

HRID 714526 reaction equation
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1.C(O)(=O)C.[C:14]([N:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)([O:16][CH2:17][CH3:18])=[O:15]>ClCCCl>[CH2:17]([O:16][C:14]([N:19]1[CH2:24][CH2:23][CH:22]([N:1]2[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]2)[CH2:21][CH2:20]1)=[O:15])[CH3:18]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 37734-Piperidinecarboxylic acidHCID 34767Ethyl 4-oxo-1-piperidinecarboxylate

Product 1

HCID 86724914HCID 86724914, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of Isonipecotic acid (8.0 g, 61.0 mmol) in DCE (80 mL) was treated with acetic acid (10.7 mL, 185 mmol) and 1-carbethoxy-4-piperidone (12.7 g, 74.3 mmol). The reaction mixture was stirred for 1 hr at 40° C. Then STAB (29.2 g, 92.8 mmol) was added, the reaction mixture was stirred at 70° C. for 6 h, cooled to rt and the solvent was removed in vacuo. The residue was purified by column chromatography (gradient 0% to 50% MeOH in CHCl3) to give 1′-(ethoxycarbonyI)-1,4′-bipiperidine-4-carboxylic acid (16.0 g, 92.2%), Intermediate 1, as an off white solid.

Workup

  1. additionThen STAB (29.2 g, 92.8 mmol) was added
  2. stirringthe reaction mixture was stirred at 70° C. for 6 h
  3. temperaturecooled to rt
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by column chromatography (gradient 0% to 50% MeOH in CHCl3)

Sources & evidence

ORD record
ord-710745b9adc14c1f9db0961595ecbcef
Source dataset
uspto-grants-2015_11
Patent number
US09187451B2

Reaction notes

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