Nitrogen → N,N-dimethyl-3-azabicyclo[3.2.1]octan-8-amine

HRID 627359Notes

Reaction equation

HRID 627359 reaction equation
C([N:8]1[CH2:14][CH:13]2[CH:15]([N:16]([CH3:18])[CH3:17])[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)C1C=CC=CC=1.N#N>CO.[Pd]>[CH3:17][N:16]([CH3:18])[CH:15]1[CH:13]2[CH2:12][CH2:11][CH:10]1[CH2:9][NH:8][CH2:14]2

Participants

5

Reactant 2

HCID 947NitrogenHCID 67355408HCID 67355408, compound

Product 1

HCID 67356379N,N-dimethyl-3-azabicyclo[3.2.1]octan-8-amineYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

3-benzyl-N,N-dimethyl-3-azabicyclo[3.2.1]octan-8-amine (80 mg, 0.45 mmol) was dissolved in MeOH (10 ml) and the atmosphere was replaced with N2 (3×). 10% Pd/C (cat.) was added and the atmosphere was replaced with H2 (3×). The resulting reaction mixture was stirred at RT at balloon pressure overnight. When TLC showed no more UV active spot the Pd/C was filtered off (always keeping wet with MeOH) and the filtrate was concentrated which gave N,N-dimethyl-3-azabicyclo[3.2.1]octan-8-amine (44 mg) in 87% yield. 1H NMR (400 MHz, MeOD) δ ppm 3.45 (d, J=12.13 Hz, 2H) 2.88 (dd, J=12.38, 2.78 Hz, 2H) 2.35 (d, J=2.02 Hz, 2H) 2.31-2.23 (m, 6H) 2.11 (t, J=4.80 Hz, 1H) 2.06-1.92 (m, 2H) 1.89-1.79 (m, 2H)

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas filtered off (
  3. concentrationwas concentrated which

Sources & evidence

ORD record
ord-96e36b4b3521467392336c9dac325db2
Source dataset
uspto-grants-2016_04
Patent number
US09309252B2

Reaction notes

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