Triethylamine → HCID 57419478, compound

HRID 2280605Notes

Reaction equation

HRID 2280605 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[C:4]([CH2:12]Br)[CH:3]=1.[CH3:14][O:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=1[CH2:24][NH2:25].C(N(CC)CC)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:10][CH:11]=1)[C:6](=[O:8])[N:25]([CH2:24][C:17]1[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:16]=1[O:15][CH3:14])[CH2:12]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5972502,4-DimethoxybenzylamineHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

Product 1

HCID 57419478HCID 57419478, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-bromo-2-(bromomethyl)benzoate (1.0 g, 3.25 mmol) and (2,4-dimethoxyphenyl)methanamine (0.65 g, 3.90 mmol) in THF (16 mL) was added triethylamine (0.91 mL, 6.5 mmol), and the resulting mixture was stirred at room temperature for 16 h. The resulting solid was filtered off, and the filtrate was concentrated in vacuo. The crude product was purified by column chromatography on silica gel using 1:4 EtOAc:hexanes as the eluent to give the title compound as a colorless solid (0.52 g, 44%).

Workup

  1. filtrationThe resulting solid was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude product was purified by column chromatography on silica gel using 1:4 EtOAc

Sources & evidence

ORD record
ord-7d2e9a2ba20b473cbca234b96892d57b
Source dataset
uspto-grants-2015_09
Patent number
US09139536B2

Reaction notes

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