Potassium Hydroxide → N-[3-{3-(piperidinomethyl)phenoxy}propyl]-2-mercaptoacetamide

HRID 1904324Notes

Reaction equation

HRID 1904324 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[CH2:17][S:18]C(=O)C)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+]>CO.O>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[CH2:17][SH:18])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 14625129HCID 14625129, compound

Product 1

HCID 10663641N-[3-{3-(piperidinomethyl)phenoxy}propyl]-2-mercaptoacetamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2.23 g of this acetamide was dissolved in a mixed solvent of 30 ml of methanol and 3 ml of water, and cooled in an ice bath. 0.48 g of 85% potassium hydroxide was added to this solution, and stirred at 0° C. for 1.5 hours. pH of the reaction solution was adjusted to 7 by adding 2N aqueous hydrochloric acid, and extraction was carried out by adding 100 ml of dichloromethane and 50 ml of water. The dichloromethane layer was washed twice with water, and dried over anhydrous magnesium sulfate. The solvent was evapoated in vacuo to obtain the captioned colorless oily N-[3-{3-(piperidinomethyl)phenoxy}propyl]-2-mercaptoacetamide. Yield: 1.86 g.

Workup

  1. temperaturecooled in an ice bath
  2. additionby adding
  3. extraction2N aqueous hydrochloric acid, and extraction
  4. additionby adding 100 ml of dichloromethane and 50 ml of water
  5. washThe dichloromethane layer was washed twice with water
  6. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-700b68cf05334e948059c7de2139b87b
Source dataset
uspto-grants-1989_06
Patent number
US04837316

Reaction notes

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