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

HRID 1790691Notes

Reaction equation

HRID 1790691 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 sodiumtriacetoxyborohydride (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-2ddcd16f5d4e40acba51d53f18999402
Source dataset
uspto-grants-2006_07
Patent number
US07071216B2

Reaction notes

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