Water → (1-Ethylpiperidin-4-yl)methanamine

HRID 1790503Notes

Reaction equation

HRID 1790503 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][NH2:17])[CH2:12][CH2:11]1)(=O)[CH3:8].O.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:7]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][NH2:17])[CH2:12][CH2:11]1)[CH3:8]

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 126870221-(4-(Aminomethyl)piperidin-1-yl)ethan-1-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 2794704(1-Ethylpiperidin-4-yl)methanamineYield 83.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Lithium aluminum hydride (1.06 g) was suspended in tetrahydrofuran (70 ml) and the resultant suspension was stirred under nitrogen atmosphere under ice cooling. Next, 1-acetyl-4-aminomethylpiperidine (4.14 g). dissolved in tetrahydrofuran (30 ml) was added thereto and the resultant mixture was stirred at room temperature for 10 min and heated under reflux overnight. Then the reaction mixtures were ice-cooled and water (1.06 ml), a 5 N aqueous solution of sodium hydroxide (1.06 ml) and further water (3.18 ml) were successively added thereto. After stirring, the mixture was diluted with ethyl acetate and the insolubles were filtered off. The residue was purified by NH-silica gel column chromatography (chloroform/methanol system) to give the title compound (3.15 g) as a pale brown oil.

Workup

  1. additionwas added
  2. temperatureheated
  3. temperatureunder reflux overnight
  4. customThen the reaction mixtures
  5. temperaturecooled
  6. filtrationthe insolubles were filtered off
  7. customThe residue was purified by NH-silica gel column chromatography (chloroform/methanol system)

Sources & evidence

ORD record
ord-73405c1cfbe74fcaa850e38e2982bcb1
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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