Piperidine → Ethyl 4-(3-Piperidin-1-ylpropoxy)benzoate

HRID 268704Notes

Reaction equation

HRID 268704 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1.[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC.CCOC(C)=O.[I-].[K+]>[N:17]1([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 3

HCID 8082PiperidineHCID 10340Sodium CarbonateHCID 18348522Ethyl 4-(3-chloropropoxy)benzoate

Product 1

HCID 17986307Ethyl 4-(3-Piperidin-1-ylpropoxy)benzoate

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
105 °C

Procedure

A stirred mixture of ethyl 4-(3-chloropropoxy)benzoate (70.0 g), piperidine (43.35 ml), sodium carbonate (45.36 g) and potassium iodide (2.37 g) in 1-butanol (650 ml) was heated at 105° C. for 16 h. The reaction was cooled to rt, diluted with EtOAc (1600 ml), washed with water (3×700 ml), saturated brine (700 ml), dried (MgSO4) and evaporated to give the title compound (D1) (82.57 g) which displayed MS and 1H NMR spectra that were identical to those of the product obtained by D1 (Method A).

Workup

  1. temperatureThe reaction was cooled to rt
  2. washwashed with water (3×700 ml), saturated brine (700 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-94fe1cbe5b864289ae81f3f0848c2cf1
Source dataset
uspto-grants-2008_11
Patent number
US07446103B2

Reaction notes

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