Sulfuric acid magnesium salt (1:1) → HCID 22137337, compound

HRID 1827519Notes

Reaction equation

HRID 1827519 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH:5]=O.[N:17]1([CH2:22][CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH2:5][NH:31][C:28]1[CH:29]=[CH:30][C:25]([O:24][CH2:23][CH2:22][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)3×HCID 64937494-(2-(Pyrrolidin-1-yl)ethoxy)anilineHCID 22137302HCID 22137302, compound

Product 1

HCID 22137337HCID 22137337, compoundYield 117.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde (0.700 g, 3.18 mmol) and 4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine (0.624 g, 3.02 mmol) in 20 mL methylene chloride was added magnesium sulfate (1.82 g, 15.12 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was filtered and concentrated. The residue was redissolved in 20 mL methylene chloride and was treated with magnesium sulfate (1.82 g, 15.12 mmol). The reaction was again stirred overnight at room temperature. The reaction was filtered and concentrated. The residue was again redissolved in 20 mL methylene chloride and was treated with magnesium sulfate (1.82 g, 15.12 mmol). The reaction was once again stirred overnight at room temperature. The reaction was filtered and concentrated. The resulting oil was dissolved in 12 mL ethanol and 6 mL methanol and was treated with sodium borohyride (0.560 g, 14.80 mmol) which was added in two portions over a period of 1 hr. The reaction was stirred at room temperature for 4 days at which time the solvent was removed in vacuo. To the residue was added water, and the mixture was extracted three times with methylene chloride. The combined organic layers were washed with saturated aqueous sodium chloride, dried (sodium sulfate), filtered, and concentrated to afford 1.46 g of the title compound. MS 411.4 (M+1)+

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was redissolved in 20 mL methylene chloride
  4. waitThe reaction was again stirred overnight at room temperature
  5. filtrationThe reaction was filtered
  6. concentrationconcentrated
  7. dissolutionThe residue was again redissolved in 20 mL methylene chloride
  8. waitThe reaction was once again stirred overnight at room temperature
  9. filtrationThe reaction was filtered
  10. concentrationconcentrated
  11. dissolutionThe resulting oil was dissolved in 12 mL ethanol
  12. addition6 mL methanol and was treated with sodium borohyride (0.560 g, 14.80 mmol) which
  13. additionwas added in two portions over a period of 1 hr
  14. stirringThe reaction was stirred at room temperature for 4 days at which time the solvent
  15. customwas removed in vacuo
  16. additionTo the residue was added water
  17. extractionthe mixture was extracted three times with methylene chloride
  18. washThe combined organic layers were washed with saturated aqueous sodium chloride
  19. dry with materialdried (sodium sulfate)
  20. filtrationfiltered
  21. concentrationconcentrated

Sources & evidence

ORD record
ord-54dd8422883242cd847d3cc30c3c5f28
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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