4-Iodoaniline → HCID 22137416, compound

HRID 1827566Notes

Reaction equation

HRID 1827566 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1.[I:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1.S([O-])([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>C(Cl)Cl.CO>[I:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][CH2:12][C:11]2[CH:14]=[CH:15][C:8]([O:7][CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)=[CH:9][CH:10]=2)=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 108934-IodoanilineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 112527364-(2-Tetrahydro-2H-pyranoxy)benzaldehyde

Product 1

HCID 22137416HCID 22137416, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(tetrahydro-pyran-2-yloxy)-benzaldehyde (9.07 g, 43.96 mmol) and 4-iodoaniline (8.87 g, 40.49 mmol) in 200 mL methylene chloride was added magnesium sulfate (26.7 g, 221.82 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered through diatomaceous earth and the filtrate was concentrated. The residue was dissolved in 150 mL ethanol and 75 mL methanol and sodium borohydride (6 g, 158.60 mmol) was added in portions over a period of 2 hr. The reaction mixture was stirred at room temperature for an additional 2 hr. The reaction mixture was quenched with water and the aqueous solution was washed three times with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated. Medium pressure silica gel chromatography (10% hexanes/ethyl acetate) followed by crystallization from methylene chloride/methanol afforded the title compound of Step A.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in 150 mL ethanol
  4. stirringThe reaction mixture was stirred at room temperature for an additional 2 hr
  5. customThe reaction mixture was quenched with water
  6. washthe aqueous solution was washed three times with methylene chloride
  7. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  8. concentrationconcentrated
  9. customMedium pressure silica gel chromatography (10% hexanes/ethyl acetate) followed by crystallization from methylene chloride/methanol

Sources & evidence

ORD record
ord-d51cb01732e942c6b3b7de0b8b258d26
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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