Dimethylformamide → 4-[3-[(3-Methylpiperidin-1-yl)methyl]phenoxy]butanamine

HRID 4650

Reaction equation

HRID 4650 reaction equation
C[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[CH2:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1.[H-].[Na+].Cl[CH2:19][CH2:20][CH2:21][C:22]#[N:23].[O-]S([O-])(=O)=O.[Na+].[Na+].[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:37]N(C=O)C>CCOCC.O>[CH3:37][CH:5]1[CH2:6][CH2:7][CH2:2][N:3]([CH2:8][C:9]2[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=2)[O:15][CH2:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH2:4]1

Participants

9

Reactant 6

HCID 6228DimethylformamideHCID 123364-ChlorobutyronitrileHCID 24436Sodium SulfateHCID 24758Sodium hydrideHCID 21226445Aluminium lithium hydrideHCID 539950293-((2-Methylpiperidin-1-yl)methyl)phenol

Product 1

HCID 140261874-[3-[(3-Methylpiperidin-1-yl)methyl]phenoxy]butanamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

5.13 g (0.025 mol) of 3-((methylpiperidin-1-yl)methyl) phenol (Example 64 a) are added to a suspension of 1.0 g (0.025 mol) of sodium hydride (60%) in absolute DMF and the mixture is stirred overnight at room temperature. After the addition of 2.58 g (0.025 mol) of 4chlorobutyronitrile, the reaction mixture is stirred at 60° C. for 7 hours, 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 H2O. After removal of the inorganic constituents by filtration and evaporation of the solvent under vacuum, 3.66 g of a pale yellow oil are left behind.

Workup

  1. stirringthe reaction mixture is stirred at 60° C. for 7 hours
  2. extractionextracted with ether
  3. washthe organic phase is washed with 5% NaOH
  4. customAfter removal of the inorganic constituents
  5. filtrationby filtration and evaporation of the solvent under vacuum, 3.66 g of a pale yellow oil
  6. waitare left behind

Sources & evidence

ORD record
ord-a74a4d08ee934a7985e29a4219f4899c
Source dataset
uspto-grants-1988_02
Patent number
US04727081

Linked notes

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