Hydrochloric Acid → N-methyl-N-piperidin-3-yl-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-amine trihydrochloride

HRID 2093338Notes

Reaction equation

HRID 2093338 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([N:14]([CH3:24])[C:15]2[CH:20]=[CH:19][N:18]=[C:17]3[NH:21][CH:22]=[CH:23][C:16]=23)[CH2:9]1)C1C=CC=CC=1.C(O)C.[ClH:28]>O.[OH-].[Pd+2].[OH-]>[ClH:28].[ClH:28].[ClH:28].[CH3:24][N:14]([CH:10]1[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]1)[C:15]1[CH:20]=[CH:19][N:18]=[C:17]2[NH:21][CH:22]=[CH:23][C:16]=12

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 59659146N-(1-benzylpiperidin-3-yl)-N-methyl-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-amine

Product 1

HCID 66663146N-methyl-N-piperidin-3-yl-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-amine trihydrochloride

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 962WaterSolvent

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.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-4cd1ce0d10d344dc937f9308ea0734b3
Source dataset
uspto-grants-2013_05
Patent number
US08445488B2

Reaction notes

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