Water → 1-(tetrahydrofuran-2-ylmethyl)piperidin-4-amine(SALTDATA: 2HCl 0.5H2O)

HRID 622680Notes

Reaction equation

HRID 622680 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][N:7]1[CH2:12][CH2:11][C:10](=[N:13]O)[CH2:9][CH2:8]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([NH2:13])[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 212915121-(2-Tetrahydrofurylmethyl)piperid-4-one oxime

Product 1

HCID 167746731-(tetrahydrofuran-2-ylmethyl)piperidin-4-amine(SALTDATA: 2HCl 0.5H2O)

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-(2-tetrahydrofurylmethyl)piperid-4-one oxime (42.5 g; 0.22 moles) in anhydrous tetrahydrofuran (700 ml) was added dropwise to a suspension of lithium aluminium hydride (24.4 g; 0.64 moles) in anhydrous tetrahydrofuran (300 ml). The reaction mixture was left with stirring at room temperature overnight and then, water (24.5 ml), 4N sodium hydroxide aqueous solution (24.5 ml) and water (73.5 ml) were successively added, filtered, the filtrates dried (Na2SO4) and brought to dryness in vacuo. The resulting oil (28 g) was distilled to give 1-(2-tetrahydrofurylmethyl)-4-aminopiperidine, boiling point 94°-98° C./0.2 mm Hg.

Workup

  1. waitThe reaction mixture was left
  2. filtrationfiltered
  3. dry with materialthe filtrates dried (Na2SO4)
  4. distillationThe resulting oil (28 g) was distilled

Sources & evidence

ORD record
ord-09d6f6e35678469784fdaaf3b40fb39a
Source dataset
uspto-grants-1988_09
Patent number
US04772618

Reaction notes

Loading…