Reaction #487566

Reaction equation

4-chloro-1H-pyrrolo[2,3-b]pyridine

1-benzyl-N-methylpiperidin-3-amine

→

orange oil

Yield 130.0%

N-(1-benzylpiperidin-3-yl)-N-methyl-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-amine

Yield 130.0%

Conditions

Workup

1. 1
   OtherThe reaction mixture was partitioned between ethyl acetate (30 mL) and sat. NaHCO3 (20 mL)
2. 2
   Washthe organic phase was washed with sat. NaCl
3. 3
   Otherdried

Procedure

A sealed melted mixture of 4-chloro-1H-pyrrolo[2,3-b]pyridine (0.18 g, 0.0012 mol) in 1-benzyl-N-methylpiperidin-3-amine (0.50 g, 0.0024 mol) was heated to 200° C. overnight. The reaction mixture was partitioned between ethyl acetate (30 mL) and sat. NaHCO3 (20 mL), and the organic phase was washed with sat. NaCl, then dried and was reduced under vacuum to give 500 mg of orange oil. The product was chromatographed with 7% MeOH/DCM, 0.7% NH4OH to give 192 mg of an orange oil (48.8% yield).

Source