Water → 4-aminocarbonyl-N-(4-propoxyphenylmethyl)piperidine

HRID 866053Notes

Reaction equation

HRID 866053 reaction equation
[NH2:1][C:2]([CH:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)=[O:3].[CH2:10]([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20]Cl)=[CH:16][CH:15]=1)[CH2:11][CH3:12].C(=O)(O)[O-].[K+].O>C1(C)C=CC=CC=1>[NH2:1][C:2]([CH:4]1[CH2:9][CH2:8][N:7]([CH2:20][C:17]2[CH:18]=[CH:19][C:14]([O:13][CH2:10][CH2:11][CH3:12])=[CH:15][CH:16]=2)[CH2:6][CH2:5]1)=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 37724-PiperidinecarboxamideHCID 516893Potassium BicarbonateHCID 122491081-(Chloromethyl)-4-propoxybenzene

Product 1

HCID 190409324-aminocarbonyl-N-(4-propoxyphenylmethyl)piperidineYield 79.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The method taught by R. A. Farr et al, J. Org. Chem. 1981, 46, 1212-1215, was used in the following two-step preparation. A vigorously stirred solution of 16.5 grams (0.129 mole) of 4-aminocarbonylpiperidine, 25.0 grams (0.135 mole) of 4-propoxyphenylmethyl chloride, and 19.4 grams (0.193 mole) of potassium bicarbonate in 200 mL of toluene was heated at reflux for 6.5 hours. The reaction mixture was then cooled, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with two portions of an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a solid residue, which was slurried in pentane and collected by filtration, yielding 28.2 grams of 4-aminocarbonyl-N-(4-propoxyphenylmethyl)piperidine, mp 142°-146° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. custom1981, 46, 1212-1215, was used in the following two-step preparation
  2. temperatureat reflux for 6.5 hours
  3. temperatureThe reaction mixture was then cooled
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with two portions of an aqueous solution saturated with sodium chloride
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure to a solid residue, which
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-0bdf3c4da8a24475917f7120ee4b3488
Source dataset
uspto-grants-1996_10
Patent number
US05569664

Reaction notes

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