Potassium Hydroxide → 3-({4-[(Piperidin-1-yl)methyl]pyridin-2-yl}oxy)propan-1-amine

HRID 1981356Notes

Reaction equation

HRID 1981356 reaction equation
Cl.NO.[OH-].[K+].CC1[N:8]([CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[C:21]([CH2:23][N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:20]=[CH:19][N:18]=2)C(C)=CC=1>C(O)C>[N:24]1([CH2:23][C:21]2[CH:20]=[CH:19][N:18]=[C:17]([O:16][CH2:15][CH2:14][CH2:13][NH2:8])[CH:22]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 20399416HCID 20399416, compound

Product 1

HCID 146251023-({4-[(Piperidin-1-yl)methyl]pyridin-2-yl}oxy)propan-1-amineYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 8.6 g of hydroxylamine hydrochloride in 26 ml of ethanol, stirred at the room temperature for 30 minutes, a solution of 2.8 g of 85% potassium hydroxide in 10 ml of 50% ethanol is added. The resulting solution is stirred 10 minutes and added with 8.7 g of 2-[3-(2,5-dimethylpyrrol-1-yl)propoxy]-4-piperidinomethylpyridine. The mixture is heated with reflux for 6 hours, filtered, washed with ethanol, acidified with N hydrochloric acid and washed twice with 30 ml of ethyl acetate. The pH of the aquoeus solution is adjusted to 8, then the solution is washed twice again with 30 ml of ethyl acetate and made clearly basic by addition of a concentrated solution of potassium hydroxide. The solution is extracted with ethyl acetate, the organic phase is dried over anhydrous sodium sulfate and the solvent is evaporated off. Thus, there is obtained 5.3 g of 3-(4-piperidinomethylpyrid-2-yloxy)propylamine as an oil.

Workup

  1. temperatureThe mixture is heated
  2. temperaturewith reflux for 6 hours
  3. filtrationfiltered
  4. washwashed with ethanol
  5. washwashed twice with 30 ml of ethyl acetate
  6. washthe solution is washed twice again with 30 ml of ethyl acetate
  7. additionmade clearly basic by addition of a concentrated solution of potassium hydroxide
  8. extractionThe solution is extracted with ethyl acetate
  9. dry with materialthe organic phase is dried over anhydrous sodium sulfate
  10. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-2cd4e4b38f7e497eb99c33325bbebb4f
Source dataset
uspto-grants-1985_04
Patent number
US04514408

Reaction notes

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