Dimethylamine, hydrochloride → HCID 57905868, compound

HRID 1670140Notes

Reaction equation

HRID 1670140 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5](O)=[O:6].C1[CH2:16][N:15]([P+](Br)(N2CCCC2)N2CCCC2)[CH2:14]C1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.Cl.CNC>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([N:15]([CH3:16])[CH3:14])=[O:6]

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 157355113-Bromo-5-hydroxybenzoic acid

Product 1

HCID 57905868HCID 57905868, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-bromo-5-hydroxy-benzoic acid (2.0 g, 9.25 mmol), PyBroP (7.7 g, 18.5 mmol) and diisopropylethylamine (6.4 mL, 37 mmol) in DMF (50 mL) was added dimethylamine hydrochloride (1.51 g, 18.5 mmol). The reaction mixture was stirred at room temperature for 6 h. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude material was purified by column chromatography (Isco™ 120 g) using ethyl acetate as eluting solvent to give the title compound (1.5 g, 67%) as a white solid.

Workup

  1. washwashed with brine
  2. extractionThe organic extract
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by column chromatography (Isco™ 120 g)
  6. washas eluting solvent

Sources & evidence

ORD record
ord-c06fd3b68fcf411ba8d7996494755ebd
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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