Water → {1-Azabicyclo[2.2.2]octan-3-yl}methanamine

HRID 1721839Notes

Reaction equation

HRID 1721839 reaction equation
[C:1]([CH:3]1[CH:8]2[CH2:9][CH2:10][N:5]([CH2:6][CH2:7]2)[CH2:4]1)#[N:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[NH2:2][CH2:1][CH:3]1[CH:8]2[CH2:9][CH2:10][N:5]([CH2:6][CH2:7]2)[CH2:4]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 1428651-Azabicyclo(2.2.2)octane-3-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 12603059{1-Azabicyclo[2.2.2]octan-3-yl}methanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-cyanoquinuclidine (3.0g) was added to a stirred suspension of LiAlH4 (1.1g) in dry THF (250ml) and the reaction heated to reflux for 3h. On cooling the reaction, water (1ml), 2.5N NaOH solution (1.5ml) and then water (2.5ml) were added carefully and the solids removed by filtration. Evaporation of the filtrate gave the title compound, D1 (3.1g) as an oil.

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 3h
  3. temperatureOn cooling
  4. customthe solids removed by filtration
  5. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-2a4ed43c3b7645fea56bdf1be2364109
Source dataset
uspto-grants-1989_08
Patent number
US04853376

Reaction notes

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