Water → Quinolizidin-2-ylmethylamine

HRID 1458625Notes

Reaction equation

HRID 1458625 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([CH:9]1[CH2:18][CH2:17][N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:10]1)#[N:8].O.[OH-].[Na+]>C1COCC1>[CH2:10]1[CH:11]2[N:16]([CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:17][CH2:18][CH:9]1[CH2:7][NH2:8]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 125773752-CyanoquinolizidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 82413010Quinolizidin-2-ylmethylamineYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred suspension of lithium aluminium hydride (400 mg, 0.010 mole) in THF (20 ml) at room temperature under nitrogen was treated with a solution of eq-2-cyanoquinolizidine (E. Koshinaka et al, Yakugaku Zasshi 1980, 100, 88) in THF (3 ml) and the mixture then heated under reflux for 20 minutes. The mixture was allowed to cool then treated cautiously with water (0.4 ml), 10% NaOH solution (0.4 ml) and water (1.2 ml). The resulting mixture was filtered and the filtrate concentrated in vacuo. The residue was distilled in a Kugelrohr apparatus to afford the title compound (D13) as a colourless oil (700 mg, 97%).

Workup

  1. temperaturethe mixture then heated
  2. temperatureunder reflux for 20 minutes
  3. temperatureto cool
  4. filtrationThe resulting mixture was filtered
  5. concentrationthe filtrate concentrated in vacuo
  6. distillationThe residue was distilled in a Kugelrohr apparatus

Sources & evidence

ORD record
ord-01baf875a3f44ef8b48edbb0157c7309
Source dataset
uspto-grants-1998_12
Patent number
US05852014

Reaction notes

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