1-benzyl-4-(N-methyl-8-azabicyclo[3,2,1]oct-3-yl)-piperazine → 8-Methyl-3-(piperazin-1-yl)-8-azabicyclo[3.2.1]octane

HRID 366958Notes

Reaction equation

HRID 366958 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:20][CH:19]3[N:21]([CH3:22])[CH:16]([CH2:17][CH2:18]3)[CH2:15]2)[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH3:22][N:21]1[CH:19]2[CH2:18][CH2:17][CH:16]1[CH2:15][CH:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[CH2:20]2

Participants

4

Reactant 1

HCID 28463331-benzyl-4-(N-methyl-8-azabicyclo[3,2,1]oct-3-yl)-piperazine

Product 1

HCID 154797638-Methyl-3-(piperazin-1-yl)-8-azabicyclo[3.2.1]octane

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-benzyl-4-(N-methyl-8-azabicyclo[3,2,1]oct-3-yl)-piperazine (4.75 g, 15.88 mmol) in 50 ml methanol was hydrogenated at a pressure of 2.0 atm in the presence of 20% palladium hydroxide on carbon (470 mg) for 30 h. The mixture was then filtered through a pad of celite. The filtrate was concentrated to afford a pale yellow solid quantitatively, which is pure enough for subsequent use.

Workup

  1. filtrationThe mixture was then filtered through a pad of celite
  2. concentrationThe filtrate was concentrated
  3. customto afford a pale yellow solid quantitatively

Sources & evidence

ORD record
ord-fd9884bc63034b0cbb7cb4c9e15b706f
Source dataset
uspto-grants-2000_10
Patent number
US06131226

Reaction notes

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