Sodium Hydroxide → 3-Isopropyl-3,7-diazabicyclo[3.3.1]nonane

HRID 1195221Notes

Reaction equation

HRID 1195221 reaction equation
C([N:8]1[CH2:15][CH:14]2[CH2:16][CH:10]([CH2:11][N:12]([CH:17]([CH3:19])[CH3:18])[CH2:13]2)[CH2:9]1)C1C=CC=CC=1.[OH-].[Na+]>CO.O.[Pd]>[CH:17]([N:12]1[CH2:13][CH:14]2[CH2:16][CH:10]([CH2:9][NH:8][CH2:15]2)[CH2:11]1)([CH3:19])[CH3:18]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 99506987-Benzyl-3-isopropyl-3,7-diazabicyclo[3.3.1]nonane

Product 1

HCID 150358373-Isopropyl-3,7-diazabicyclo[3.3.1]nonane

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A 200-mL, three-necked, round-bottomed flask was equipped with a magnetic stirrer, a heating mantle, a condenser with a N2 inlet, and two glass stoppers. To a stirred mixture of amine (30) (5.53 g, 21.4 mmol) and 10% Pd/C (0.64 g, 30 mg/mmol of amine) in CH3OH (80 mL) was added anhydrous HCO2NH4 (3.37 g, 53.5 mmol) in one portion. Stirring the mixture at reflux under N2 for 30 min, cooling the new mixture to RT, and filtering through a celite pad was followed by concentration of the resulting solution to give a viscous oil. The oil was then dissolved in H2O (80 mL) and the pH was adjusted to ~12 by the addition of 10% NaOH. Combined extracts (CH2Cl2, 4×40 mL) of the aqueous solution were dried, filtered, and concentrated (rotary evaporator then vacuum pump, 10 min, RT/0.2 mm Hg) to give amine (31) as a light oil (3.35 g, 93.0%) which was used without further purification. IR (film) cm-1 3315 (N--H), 2965, 2900, 2850, 2790, 2760, 2725 (C--H); 1H NMR (DCCl3) δ1.01 (d, 6H, CH3, J=6.7 Hz), 1.60-1.67 [m, 3H, H(1,5) and H(9)], 2.53-2.59 [m, 3H, ring protons and CH(CH3)2 ], 2.90-3.06 [m, 6H, ring protons], 3.56 (bs, 1H, N--H); 13C NMR (DCCl3) ppm 18.12 (CH3), 30.04 [C(1,5)], 33.62 [C(9)], 52.86 [C(6,8)], 54.59 [CH(CH3)2 ], 54.65 [C(2,4)].

Workup

  1. customA 200-mL, three-necked, round-bottomed flask was equipped with a magnetic stirrer
  2. additionwas added anhydrous HCO2NH4 (3.37 g, 53.5 mmol) in one portion
  3. temperatureat reflux under N2 for 30 min
  4. filtrationfiltering through a celite pad
  5. customto give a viscous oil
  6. dry with materialCombined extracts (CH2Cl2, 4×40 mL) of the aqueous solution were dried
  7. filtrationfiltered
  8. concentrationconcentrated (
  9. customrotary evaporator

Sources & evidence

ORD record
ord-30ee8b3c07f04a0298b943b7d577c6b3
Source dataset
uspto-grants-1992_05
Patent number
US05110933

Reaction notes

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