Benzylamine → Benzyl-(3-methoxy-4-nitro-benzyl)amine

HRID 1019752Notes

Reaction equation

HRID 1019752 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([O:12][CH3:13])[CH:4]=1.C(N(CC)CC)C.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH2:21]([NH:28][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([O:12][CH3:13])[CH:4]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 126216043-Methoxy-4-nitrobenzyl bromide

Product 1

HCID 22046378Benzyl-(3-methoxy-4-nitro-benzyl)amineYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(bromomethyl)-2-methoxy-1-nitrobenzene (1.0 g, 4.06 mmol) in THF (15 ml), triethylamine (1.23 g, 12.19 mmol) and benzyl amine (1.3 g, 12.19 mmol) were added at RT and the reaction was stirred for 2 hours. The reaction mixture was partitioned between water (50 ml) and EtOAc (25 ml) and the separated aqueous layer was extracted with EtOAc (15 ml). The combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on neutral silica gel using 15-25% EtOAc in hexane to give the title compound (1.0 g, 91%).

Workup

  1. customThe reaction mixture was partitioned between water (50 ml) and EtOAc (25 ml)
  2. extractionthe separated aqueous layer was extracted with EtOAc (15 ml)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography on neutral silica gel using 15-25% EtOAc in hexane

Sources & evidence

ORD record
ord-34f6a77ac2c04cc8a2edee44b28081cc
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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