3,4-dihydro-2H-pyran → N-ethyl-N-[2-(tetrahydropyran-2-yl)oxyethyl]-4-bromoaniline

HRID 356224Notes

Reaction equation

HRID 356224 reaction equation
[CH2:1]([N:3]([CH2:11][CH2:12][OH:13])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)[CH3:2].[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH2:1]([N:3]([CH2:11][CH2:12][O:13][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][O:14]1)[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 161440Pyridine 4-methylbenzene-1-sulfonateHCID 516892Sodium BicarbonateHCID 18941473N-Ethyl-N-(beta-hydroxyethyl)-4-bromoaniline

Product 1

HCID 18941483N-ethyl-N-[2-(tetrahydropyran-2-yl)oxyethyl]-4-bromoaniline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

14.7 g (60.3 mmols) of N-ethyl-N-(2-hydroxyethyl)-4-bromoaniline, 90 ml of chloroform, 10.68 ml (2.0-fold equivalent weight) of 3,4-dihydro-2H-pyran and 0.76 g (0.05-fold equivalent weight) of pyridine p-toluenesulfonate were mixed, and the mixture obtained was heated at 70° C. for 1.5 hours in an atmosphere of argon. Thereafter, a saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution obtained, which was then extracted with chloroform (200 ml×2). The organic layer thus formed was washed with a saturated aqueous sodium hydrogencarbonate solution, which was then dried with anhydrous magnesium sulfate and thereafter concentrated. The residue thus obtained was purified by silica gel column chromatography (developing system: chloroform) to obtain 18.90 g of N-ethyl-N-[2-(tetrahydropyran-2-yl)oxyethyl]-4-bromoaniline (yield: quantitative; a colorless oily liquid).

Workup

  1. customthe mixture obtained
  2. customobtained
  3. extractionwhich was then extracted with chloroform (200 ml×2)
  4. customThe organic layer thus formed
  5. washwas washed with a saturated aqueous sodium hydrogencarbonate solution, which
  6. dry with materialwas then dried with anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue thus obtained
  9. customwas purified by silica gel column chromatography (developing system: chloroform)

Sources & evidence

ORD record
ord-b2c959a9a8bd4a0dac1f7aab1d432dec
Source dataset
uspto-grants-1998_11
Patent number
US05834575

Reaction notes

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