Water → N-Methyl-4-benzyloxy-2-fluoroaniline

HRID 853547

Reaction equation

HRID 853547 reaction equation
N1([CH2:10][NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][C:13]=2[F:26])C2C=CC=CC=2N=N1.[BH4-].[Na+].O.C(OCC)(=O)C.O1CCCC1>CN(C)C=O.CO.C(O)C>[CH3:10][NH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:14][C:13]=1[F:26]

Participants

8

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydride2×HCID 21939870Tetrahydrofuran ethyl acetateHCID 22936313N-{1-(1H-Benzotriazolyl)methyl}-4-benzyloxy-2-fluoroaniline

Product 1

HCID 22936658N-Methyl-4-benzyloxy-2-fluoroanilineYield 64.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

After dissolving N-{1-(1H-benzotriazolyl)methyl}-4-benzyloxy-2-fluoroaniline (14.13 g, 40.56 mmol) in N,N-dimethylformamide (200 ml), methanol (150 ml) and ethanol (50 ml), there was added sodium borohydride (3.06 g, 81.12 mmol) and the mixture was stirred for 2.5 hours at room temperature. There was further added sodium borohydride (0.78 g, 20.28 mmol), and the mixture was stirred for 13.5 hours at room temperature. Water was added to the reaction solution, extraction was performed with ethyl acetate-tetrahydrofuran, the extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was adsorbed onto silica gel and purified by silica gel column chromatography (hexane-ethyl acetate system) to obtain the title compound (5.98 g, 26.31 mmol, 64.87%) as light yellow crystals.

Workup

  1. stirringthe mixture was stirred for 13.5 hours at room temperature
  2. washthe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. custompurified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-29db2766656c438a89f5b3a2b6d06772
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Linked notes

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