Reaction #487567

ord-1255f5b7c872423bb3640fca0206620b

Reaction equation

CN(c1ccnc2[nH]ccc12)C1CCCN(Cc2ccccc2)C1
N-(1-benzylpiperidin-3-yl)-N-methyl-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-amine
CCO
ethanol
Cl
hydrogen chloride
CN(c1ccnc2[nH]ccc12)C1CCCNC1.Cl.Cl.Cl
orange oil
CN(c1ccnc2[nH]ccc12)C1CCCNC1.Cl.Cl.Cl
N-methyl-N-piperidin-3-yl-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-amine trihydrochloride

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    FiltrationThe reaction mixture was filtered
  2. 2
    Washwashed with MeOH
  3. 3
    ConcentrationThe filtrate was concentrated under vacuum

Procedure

A degassed mixture of N-(1-benzylpiperidin-3-yl)-N-methyl-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-amine (0.17 g, 0.00053 mol) and palladium hydroxide (0.15 g, 0.00011 mol) in ethanol (3.5 mL, 0.060 mol) and 3.0 M of hydrogen chloride in water (0.40 mL) was stirred under an atmosphere of hydrogen over 2.5 days. The reaction mixture was filtered and washed with MeOH. The filtrate was concentrated under vacuum to give 92 mg of orange oil.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08741895B2uspto-grants-2014_06