Methylamine → 1-([1,1'-Biphenyl]-4-yl)-N-methylmethanamine

HRID 2165106Notes

Reaction equation

HRID 2165106 reaction equation
[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[CH3:15][NH2:16]>ClCCl.C(O)C>[CH3:15][NH:16][CH2:7][C:4]1[CH:5]=[CH:6][C:1]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 76689(1,1'-Biphenyl)-4-carboxaldehyde

Product 1

HCID 47223691-([1,1'-Biphenyl]-4-yl)-N-methylmethanamine

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

10 g of 4-Biphenylcarbaldehyde and 40 ml of 33% ethanolic methylamine are stirred overnight at room temperature with a 4 Å molecular sieve. The mixture is filtered and concentrated under vacuum. The residue is treated in 60 ml of ethanol with 2 g of sodium borohydride and stirred for 3 hours. The solvent is removed under vacuum, the residue partitioned between ether and water and the organic phase dried and concentrated. The pure base is obtained as an oil following chromatography on silica gel with dichloromethane/ethanol=9/1 as eluant.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated under vacuum
  3. additionThe residue is treated in 60 ml of ethanol with 2 g of sodium borohydride
  4. customThe solvent is removed under vacuum
  5. customthe residue partitioned between ether and water
  6. customthe organic phase dried
  7. concentrationconcentrated
  8. customThe pure base is obtained as an oil

Sources & evidence

ORD record
ord-73639d7126cd4223989c2ed29fbf73f6
Source dataset
uspto-grants-1990_07
Patent number
US04939148

Reaction notes

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