Methanamine, hydrochloride (1:1) → 1-{1-[(4-Methoxyphenyl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}-N-methylmethanamine hydrochloride

HRID 554387Notes

Reaction equation

HRID 554387 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:15][C:14]([CH:23]=O)=[CH:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[Cl-:25].C[NH3+].[C:28]([BH3-])#[N:29].[Na+]>CO>[ClH:25].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:15][C:14]([CH2:23][NH:29][CH3:28])=[CH:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11637Methanamine, hydrochloride (1:1)HCID 5003444Sodium cyanoborohydrideHCID 862329231-[(4-Methoxyphenyl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehyde

Product 1

HCID 669247241-{1-[(4-Methoxyphenyl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}-N-methylmethanamine hydrochlorideYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[(4-Methoxyphenyl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehyde (240 mg) was dissolved in methanol (5 mL), methylammonium chloride (856 mg) and sodium cyanoborohydride (131 mg) were added, and the mixture was stirred at room temperature for 18 hr. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate was added to the residue; and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=6:1→ethyl acetate). The obtained oil was dissolved in ethyl acetate (5 mL), 4 mol/L hydrogen chloride-ethyl acetate solution (0.5 mL) was added, and the mixture was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give the title compound as colorless crystals (yield 148 mg, 54%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate
  2. additionwas added to the residue
  3. extractionand the mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=6:1→ethyl acetate)
  8. dissolutionThe obtained oil was dissolved in ethyl acetate (5 mL)
  9. addition4 mol/L hydrogen chloride-ethyl acetate solution (0.5 mL) was added
  10. concentrationthe mixture was concentrated under reduced pressure
  11. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-dce3d0a571484fc5932502c75d8fefc6
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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