4-Fluorobenzylamine → Benzeneethanamine, N-[(4-fluorophenyl)methyl]-3-nitro-

HRID 1019773Notes

Reaction equation

HRID 1019773 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][CH:11]=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=1.[BH4-].[Na+].C(=O)(O)[O-].[Na+]>CO.C(O)(=O)C>[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH:19][CH2:11][CH2:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 673264-FluorobenzylamineHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 115284082-(3-nitrophenyl)acetaldehyde

Product 1

HCID 67468911Benzeneethanamine, N-[(4-fluorophenyl)methyl]-3-nitro-Yield 40%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

2-(3-nitrophenyl)acetaldehyde (1.2 g, 7.33 mmol) was dissolved in methanol (50 mL) and 4-fluorobenzylamine (1.88 g, 14.67 mmol) was added at 15° C. followed by 1-2 drops of glacial acetic acid. The reaction was stirred at room temperature for 2 hours then sodium borohydride (0.14 g, 3.6 6 mmol) was added in lots at 0-10° C. and the solution allowed to warm to room temperature and stirred for a further 2 hours. The reaction mixture was poured into sodium bicarbonate solution (75 mL) and stirred for 15 minutes. The mixture was extracted with EtOAc (2×60 mL) then the combined organic extracts were washed with brine (50 mL) and dried (Na2SO4). The solvents were removed under reduced pressure to afford the crude compound which was purified by column chromatography on neutral silica gel using 1-2% methanol in DCM to afford the title compound (0.793 g, 40%).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for a further 2 hours
  3. stirringstirred for 15 minutes
  4. extractionThe mixture was extracted with EtOAc (2×60 mL)
  5. washthe combined organic extracts were washed with brine (50 mL)
  6. dry with materialdried (Na2SO4)
  7. customThe solvents were removed under reduced pressure
  8. customto afford the crude compound which
  9. customwas purified by column chromatography on neutral silica gel using 1-2% methanol in DCM

Sources & evidence

ORD record
ord-83485fe24e5247f49a23b076e4a07433
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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