Reaction #166409

Reaction equation

chloroacetyl chloride

compound 397

4-(aminomethyl)-1-benzylpiperidin-4-ol

triethylamine

→

compound 398

Yield 78.4%

N-((1-benzyl-4-hydroxypiperidin-4-yl)methyl)-2-chloroacetamide

Yield 78.4%

Solvents

DCM

water

dichloromethane

Conditions

Workup

1. 1
   Extractionextracted with DCM twice
2. 2
   DryingThe combined organics were dried over Na2SO4
3. 3
   Concentrationconcentrated in vacuo

Procedure

To a solution of compound 397 (39.7 g, 180 mmol) in dichloromethane (350 mL) was added triethylamine (50.0 mL, 359 mmol), followed by dropwise addition of chloroacetyl chloride (16.5 mL, 207 mmol) over 15 minutes. The resulting solution was stirred at room temperature for 1.25 hours. The crude mixture was diluted with DCM and water, and extracted with DCM twice. The combined organics were dried over Na2SO4 and concentrated in vacuo to give compound 398 (41.9 g, 78%). LCMS-ESI (POS), M/Z, M+1: Found 297.1, Calculated 297.1.

Source