Dimethylamine → 1-(3-Methoxy-4-nitrophenyl)-N,N-dimethylmethanamine

HRID 2205918Notes

Reaction equation

HRID 2205918 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.[CH2:14]([N:16](CC)[CH2:17]C)C.CNC>C1COCC1>[CH3:13][O:12][C:5]1[CH:4]=[C:3]([CH2:2][N:16]([CH3:17])[CH3:14])[CH:8]=[CH:7][C:6]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8471TriethylamineHCID 126216043-Methoxy-4-nitrobenzyl bromide

Product 1

HCID 220464651-(3-Methoxy-4-nitrophenyl)-N,N-dimethylmethanamineYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 4-(bromomethyl)-2-methoxy-1-nitrobenzene (Preparation 104, 0.2 g, 0.813 mmol) in dry THF (5 ml), was added triethylamine (0.1 g, 1 mmol) followed by a solution of dimethylamine in THF (0.5 ml of a 2M solution, 1 mmol). After stirring for 1 hour at room temperature, the solvent was removed in vacuum and the crude product was purified by silica gel column chromatography eluting with 10% methanol in ethyl acetate to afford the title compound as a white powder (0.16 g, 94%).

Workup

  1. customthe solvent was removed in vacuum
  2. customthe crude product was purified by silica gel column chromatography
  3. washeluting with 10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-95f977f51e534eabbf4a657d090ac1ed
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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