Water → {1-Azabicyclo[3.3.1]nonan-5-yl}methanamine

HRID 5366

Reaction equation

HRID 5366 reaction equation
[N:1]12[CH2:9][C:5]([C:10]([NH2:12])=O)([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3][CH2:2]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.O.[OH-].[Na+]>O1CCCC1.CCOCC>[N:1]12[CH2:9][C:5]([CH2:10][NH2:12])([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3][CH2:2]2

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 197959811-Azabicyclo[3.3.1]nonane-5-carboxamideHCID 68718528lithium aluminium hydride THF

Product 1

HCID 19795986{1-Azabicyclo[3.3.1]nonan-5-yl}methanamineYield 77%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 1-azabicyclo[3.3.1]nonane-5-carboxamide (1.80 g, 10.7 mmol) in anhydrous tetrahydrofuran (10 mL) under nitrogen was treated (via syringe) with 1.0N lithium aluminum hydride/tetrahydrofuran (25 mL, 25 mmol), and the mixture was refluxed for 4 hours and cooled (0° C.). The mixture was treated carefully dropwise sequentially with water (1 mL), 15% sodium hydroxide (1 mL), and water (3 mL). Ether (50 mL) was added, the mixture was filtered through Celite, and the filter cake was washed with ether. The filtrate was concentrated in vacuo to afford 1.27 g (77%) of colorless oil.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. filtrationthe mixture was filtered through Celite
  3. washthe filter cake was washed with ether
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0445a3a91b3b46b584c36be6a9648625
Source dataset
uspto-grants-1993_09
Patent number
US05244907

Linked notes

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