Sodium Sulfate → 3-{3-[(3-Methylpiperidin-1-yl)methyl]phenoxy}propan-1-amine

HRID 4649

Reaction equation

HRID 4649 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([CH2:8][C:9]2[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=2)[CH2:3]1.[H-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CN(C=O)C.CCOCC.O>[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([CH2:8][C:9]2[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=2)[O:15][CH2:1][CH2:2][CH2:3][NH2:4])[CH2:3]1

Participants

8

Reactant 4

HCID 24436Sodium SulfateHCID 24758Sodium hydrideHCID 133646663-[(3-Methylpiperidin-1-yl)methyl]phenolHCID 21226445Aluminium lithium hydride

Product 1

HCID 140261883-{3-[(3-Methylpiperidin-1-yl)methyl]phenoxy}propan-1-amine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

5.13 g (0.025 mol) of 3-[(3-Methylpiperidin-1-yl) methyl]phenol are introduced into a suspension of 1.0 g (0.025 mol) of sodium hydride (60%) in absolute DMF and stirred overnight at room temperature. After the addition of 2.23 g (0.025 mol) of 3-chloropropionic acid nitrile, the reaction mixture is stirred for 7 hours at 60° C. and then poured into ice water and extracted with ether, and the organic phase is washed with 5% NaOH. After dehydration over Na2SO4, the ethereal phase is introduced dropwise into a suspension of 1.14 g (0.03 mol) of LiAlH4 in absolute ether and then hydrolysed with 2.2 ml of H2O. After filtration and removal of solvent by evaporation under vacuum, 2.96 g of a pale yellow oil are left behind.

Workup

  1. stirringthe reaction mixture is stirred for 7 hours at 60° C.
  2. extractionextracted with ether
  3. washthe organic phase is washed with 5% NaOH
  4. filtrationAfter filtration and removal of solvent
  5. customby evaporation under vacuum, 2.96 g of a pale yellow oil
  6. waitare left behind

Sources & evidence

ORD record
ord-055eb18c1384484c97946551c03e5d3e
Source dataset
uspto-grants-1988_02
Patent number
US04727081

Linked notes

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