1,2-Dichloroethane → HCID 14625129, compound

HRID 1904323Notes

Reaction equation

HRID 1904323 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:19]([S:22][CH2:23][C:24](O)=[O:25])(=[O:21])[CH3:20].C(Cl)CCl.O>ClCCl>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:24](=[O:25])[CH2:23][S:22][C:19](=[O:21])[CH3:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 14485Acetic acid, 2-(acetylthio)-HCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine

Product 1

HCID 14625129HCID 14625129, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.94 g of 3-{3-(piperidinomethyl)phenoxy}propylamine was dissolved in 80 ml of dichloromethane, and stirred under cooling in an ice bath. 1.60 g of 2-(acetylthio)acetic acid and 2.26 g of EDC were added to this solution, and stirred at 0° C. for 30 minutes then at room temperature overnight. 100 ml of water and 50 ml of dichloromethane were added to the reaction solution, and extraction was carried out. The dichloromethane layer was washed twice with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, and the residue was purified by silica gel column chromatography using methanol:dichloromethane=1:15 as developing solvent to obtain the colorless oily N-[3-{3-(piperidinomethyl)phenoxy}propyl]-2-(acetylthio)acetamide. Yield: 2.23 g.

Workup

  1. temperatureunder cooling in an ice bath
  2. stirringstirred at 0° C. for 30 minutes
  3. customat room temperature
  4. customovernight
  5. washThe dichloromethane layer was washed twice with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated in vacuo
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9a69c6c3a46444bc8a50cce25ff383bd
Source dataset
uspto-grants-1989_06
Patent number
US04837316

Reaction notes

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