p-Nitroacetophenone → [(4-Nitrophenyl)ethyl]benzylamine

HRID 2070284Notes

Reaction equation

HRID 2070284 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13]1([CH2:19][NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][NH:20][CH2:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7487p-NitroacetophenoneHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 10999672[(4-Nitrophenyl)ethyl]benzylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(4-nitrophenyl)ethan-1-one (1 eq) and phenylmethylamine (1 eq) in methanol was added sodium triacetoxyborohydride (1.2 eq). The resulting mixture was stirred at ambient temperature for 16 h. The mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was concentrated and preparative purification yielded [(4-nitrophenyl) ethyl]benzylamine. MS: MH+=256.

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between ethyl acetate and water
  3. concentrationThe organic layer was concentrated
  4. custompreparative purification

Sources & evidence

ORD record
ord-13fa14dfc3c54749aec3f9a43a06486b
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

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