Water → 1-[4-(Aminomethyl)piperidin-1-yl]butan-2-ol

HRID 965808Notes

Reaction equation

HRID 965808 reaction equation
[O:1]=[C:2]([CH2:13][CH3:14])[CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]([NH2:12])=O)[CH2:6][CH2:5]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH2:12][CH2:10][CH:7]1[CH2:6][CH2:5][N:4]([CH2:3][CH:2]([OH:1])[CH2:13][CH3:14])[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 223132701-(2-Oxobutyl)piperidine-4-carboxamide

Product 1

HCID 223132691-[4-(Aminomethyl)piperidin-1-yl]butan-2-olYield 109.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 1-(2-oxobutyl)piperidine-4-carboxamide (Example 13, Step 1, 1.60 g, 8.07 mmol) in tetrahydrofuran (200 mL) was added portionwise lithium aluminum hydride (920 mg, 24.21 mmol) at room temperature. The resulting mixture was refluxed for 5 h and cooled to room temperature. The mixture was treated with water (1.8 mL), 2N aqueous sodium hydroxide (3.6 mL) and water (1.8 mL). The mixture was filtered through a pad of Celite and the filtrate was concentrated in vacuo to afford 1.64 g (97%) of the title compound as colorless oil.

Workup

  1. temperatureThe resulting mixture was refluxed for 5 h
  2. filtrationThe mixture was filtered through a pad of Celite
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-65fb92c34e6840a38034c5283ce71cac
Source dataset
uspto-grants-2005_10
Patent number
US06951867B2

Reaction notes

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