Piperidine → HCID 86660297, compound

HRID 453679Notes

Reaction equation

HRID 453679 reaction equation
[O:1]=[C:2]([O:23][C@@H:24]1[CH:29]2[CH2:30][CH2:31][N:26]([CH2:27][CH2:28]2)[CH2:25]1)[CH:3]([NH:10][C:11]1[CH:12]=[C:13]([CH:20]=[CH:21][CH:22]=1)[C:14]([O:16]CC=C)=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.N1CCCCC1>C1COCC1>[O:1]=[C:2]([O:23][CH:24]1[CH:29]2[CH2:30][CH2:31][N:26]([CH2:27][CH2:28]2)[CH2:25]1)[C@H:3]([NH:10][C:11]1[CH:12]=[C:13]([CH:20]=[CH:21][CH:22]=1)[C:14]([OH:16])=[O:15])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 58556916HCID 58556916, compound

Product 1

HCID 86660297HCID 86660297, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of allyl 3-(2-oxo-1-phenyl-2-((R)-quinuclidin-3-yloxy)ethyl-amino)benzoate (I4) (1.40 g, 3.33 mmol) in dry THF (45 ml), were added tetrakis-(triphenylphosphine)palladium(0) (1.15 g, 1.00 mmol) and piperidine (0.99 ml, 1.00 mmol) and the reaction mixture was stirred at 60° C. for 1.5 hours. The solvent was removed in vacuo and the crude was purified by flash chromatography (DCM/MeOH=9/1 to MeOH) to obtain (R)-3-(2-oxo-1-phenyl-2-(quinuclidin-3-yloxy)ethylamino)benzoic acid (500 mg, 39.5% yield).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude was purified by flash chromatography (DCM/MeOH=9/1 to MeOH)

Sources & evidence

ORD record
ord-c7d38668460c45f8b40e6ec7172f4c43
Source dataset
uspto-grants-2013_07
Patent number
US08492548B2

Reaction notes

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