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

HRID 555237Notes

Reaction equation

HRID 555237 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-443751ddc12044f786c75a91e570df9c
Source dataset
uspto-grants-2011_11
Patent number
US08053433B2

Reaction notes

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