Reaction #1265415

Reaction equation

3-chloropropanoyl chloride

3,4-dihydro-1H-isoquinoline

→

product

Yield 59.5%

3-Chloro-1-(3,4-dihydro-1H-isoquinolin-2-yl)propan-1-one

Yield 59.5%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Filtrationfiltered
2. 2
   Concentrationconcentrated in vacuo
3. 3
   Otherfollowed by purification by flash chromatography on silicagel (eluent: ethyl acetate/heptane 1:1)

Procedure

A solution of 3-chloropropanoyl chloride (10.5 g) in tetrahydrofuran (400 mL) was cooled down to 6° C. followed by the addition of a solution of 3,4-dihydro-1H-isoquinoline (10.0 g). The resulting mixture was stirred at 10° C. for 30 min, filtered and concentrated in vacuo. The residue was subjected to a standard aqueous work up procedure followed by purification by flash chromatography on silicagel (eluent: ethyl acetate/heptane 1:1) to give the product as a colourless oil (10 g).

Source