Sodium Hydroxide → (1-Propylpiperidin-4-yl)methanamine

HRID 1634747Notes

Reaction equation

HRID 1634747 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([NH2:12])=O)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[NH2:12][CH2:10][CH:7]1[CH2:8][CH2:9][N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 18678413HCID 18678413, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 3164324(1-Propylpiperidin-4-yl)methanamineYield 81.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-propylpiperidine-4-carboxamide (1.2 g, 7.06 mmol) in 50 mL THF was treated in one portion with LAH (0.98 g, 14.2 mmol). The mixture was heated at reflux for 2 hours. On cooling the excess LAH was decomposed by the stepwise addition of H2O, 1N NaOH, H2O and Na2SO4 (v/v/v/w-1;1;3;12.5 based on 1 gram of LAH). After stirring for 10 min the solids were filtered and washed with EtOAc. The solvent was removed (rotovap) to give 0.9 g of title compound as a yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. filtrationwere filtered
  4. washwashed with EtOAc
  5. customThe solvent was removed (rotovap)

Sources & evidence

ORD record
ord-13d8690dc7584548a6fb2594a052e01e
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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