Sodium Iodide → Methyl 4-(3-piperidin-1-ylpropoxy)benzoate

HRID 251443Notes

Reaction equation

HRID 251443 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O-:12])=[O:11])=[CH:8][CH:7]=1.[C:15](=O)([O-])[O-].[K+].[K+].[I-].[Na+].[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>C(#N)C>[N:23]1([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:14]=[CH:13][C:9]([C:10]([O:12][CH3:15])=[O:11])=[CH:8][CH:7]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 866211874-(3-Chloropropoxy)benzoate

Product 1

HCID 9817068Methyl 4-(3-piperidin-1-ylpropoxy)benzoateYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(3-chloropropoxy)benzoate ax13 (2.01 g, 8.79 mmol, 1 eq), potassium carbonate (2.43 g, 17.6 mmol, 2 eq), sodium iodide (catalytic amount) and piperidine (1 ml, 9.67 mmol, 1.1 eq) in acetonitrile (100 ml) is stirred at reflux for 56 h. The solvent is removed under vacuum and the solid is triturated in hexane and filtered. The resulting solution is concentrated to give methyl 4-(3-piperidin-1-ylpropoxy)benzoate ax15 as a yellow oil (2.2 g).

Workup

  1. temperatureat reflux for 56 h
  2. customThe solvent is removed under vacuum
  3. customthe solid is triturated in hexane
  4. filtrationfiltered
  5. concentrationThe resulting solution is concentrated

Sources & evidence

ORD record
ord-87c59a9aebde427ba30adf45797c10d2
Source dataset
uspto-grants-2011_01
Patent number
US07863450B2

Reaction notes

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