Reaction #54452

Reaction equation

4-benzyl-4-hydroxypiperidine

β-(2-methyl-3-indolyl)propionic acid

triethylamine

ethyl chloroformate

→

1-[β-(2-methyl-3-indolyl)propionyl]-4-benzyl-4-hydroxypiperidine

Solvents

chloroform

Conditions

Workup

1. 1
   workup.ADDITIONAfter the addition
2. 2
   workup.STIRRINGThe reaction mixture was stirred for 4 hours at room temperature
3. 3
   workup.WAITto stand overnight
4. 4
   WashThe reaction product was washed thoroughly with water
5. 5
   Concentrationconcentrated to dryness
6. 6
   OtherThe residue was recrystallized from ethanol

Procedure

To a stirred solution of 5.0 g of β-(2-methyl-3-indolyl)propionic acid and 2.5 g of triethylamine in 100 ml of chloroform was added dropwise 2.7 g of ethyl chloroformate at a temperature below 0° C. After the addition was complete, stirring was continued for additional 15 minutes and thereto was added 4.7 g of 4-benzyl-4-hydroxypiperidine in several portions. The reaction mixture was stirred for 4 hours at room temperature and allowed to stand overnight. The reaction product was washed thoroughly with water and concentrated to dryness. The residue was recrystallized from ethanol to give 1-[β-(2-methyl-3-indolyl)propionyl]-4-benzyl-4-hydroxypiperidine, melting at 117°-119° C.

Source