Sodium Hydroxide → (1-Benzyl-4-piperidyl)methanamine

HRID 1634737Notes

Reaction equation

HRID 1634737 reaction equation
[CH2:1]([N:8]1[CH2:16][CH2:15][CH:11]([C:12]([NH2:14])=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[NH2:14][CH2:12][CH:11]1[CH2:10][CH2:9][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 7831561-Benzylpiperidine-4-carboxamideHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 1514444(1-Benzyl-4-piperidyl)methanamineYield 65.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 1-benzylisonipecotamide (9.0 g, 41.2 mmol) in 300 mL THF was treated portionwise with LAH (3.13 g, 82.4 mmol). The mixture was heated at reflux overnight. Upon cooling the excess LAH was decomposed by the stepwise addition of 3.13 mL H2O, 3.13 mL 1N NaOH, 9.5 mL H2O and 36 g Na2SO4. The solids were filtered and washed with ethyl acetate. The combined filtrates were concentrated in vacuo to give 5.5 g of the product as an oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. filtrationThe solids were filtered
  4. washwashed with ethyl acetate
  5. concentrationThe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-6f0c7147ca9643b783539f697faf9efd
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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