Water → HCID 19426624, compound

HRID 741571Notes

Reaction equation

HRID 741571 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[C:13](=O)[N:12]2[CH:7]([CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:6][CH2:5]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[OH:1][CH2:2][CH2:3][CH:4]1[CH2:13][N:12]2[CH:7]([CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19426627HCID 19426627, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19426624HCID 19426624, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-(2-hydroxyethyl)quinolizidin-4-one (1.4 g, 0.0071 mole) in THF (40 ml) was added to a stirred suspension of lithium aluminium hydride (0.5 g, 0.013 mole) in THF (50 ml) under nitrogen and the mixture heated under reflux for 2.5 hours, then cooled to ice bath temperature and treated dropwise with water (0.5 ml), 10% sodium hydroxide solution (0.5 ml) and water (1.5 ml). The mixture was filtered through kieselguhr and the filtrate concentrated in vacuo. The residue was distilled in a Kugelr ohr apparatus (bp approx. 140° C. at 2 mmHg) to give the title compound as a colourless oil (0.97 g, 75%).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 2.5 hours
  3. temperaturecooled to ice bath temperature
  4. filtrationThe mixture was filtered through kieselguhr
  5. concentrationthe filtrate concentrated in vacuo
  6. distillationThe residue was distilled in a Kugelr ohr apparatus (bp approx. 140° C. at 2 mmHg)

Sources & evidence

ORD record
ord-2a89f94aa79a4b1e854da02a4311ff67
Source dataset
uspto-grants-1996_09
Patent number
US05552398

Reaction notes

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