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

HRID 1915659Notes

Reaction equation

HRID 1915659 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-a8b62b3b8a834bfd9f0f9f24402710ab
Source dataset
uspto-grants-2013_12
Patent number
US08614330B2

Reaction notes

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