Methanamine, hydrochloride (1:1) → HCID 66925186, compound

HRID 554388Notes

Reaction equation

HRID 554388 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:11]=[C:10]([CH:23]=O)[CH:9]=2)=[CH:4][CH:3]=1.[Cl-].C[NH3+].[C:28]([BH3-])#[N:29].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:11]=[C:10]([CH2:23][NH:29][CH3:28])[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11637Methanamine, hydrochloride (1:1)HCID 5003444Sodium cyanoborohydrideHCID 86620772HCID 86620772, compound

Product 1

HCID 66925186HCID 66925186, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(4-Fluorophenyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrrole-3-carbaldehyde (0.49 g) was dissolved in methanol (12 mL), and methylammonium chloride (1.17 g) and sodium cyanoborohydride (0.27 g) were added. After stirring at room temperature for 18 hr, the mixture was concentrated under reduced pressure. The residue was dissolved in water, and the solution was alkalized with a saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate-methanol=5:1) to give the title compound as a colorless solid (yield 0.42 g, 82%).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate-methanol=5:1)

Sources & evidence

ORD record
ord-66d43ffa8e81467c924ce6bce91a15c9
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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