Water → 7-Methoxy-2,3,4,5-tetrahydro-1h-3-benzazepine

HRID 1713089Notes

Reaction equation

HRID 1713089 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]2[CH2:7][CH2:8][N:9](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:10][CH2:11][C:5]=2[CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 222509407-methoxy-3-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 138533487-Methoxy-2,3,4,5-tetrahydro-1h-3-benzazepine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-methoxy-3-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo-[d]azepine (6.62 g, 20 mmol) in anhydrous THF (150 ml) is added a solution of LiAlH4 in THF (1.0 M, 40 ml, 2.0 eq.). The resulting mixture is refluxed under N2 for 24 hr. To the solution at 0° C. is added water (1.52 g) very carefully with stirring, followed by the addition of sodium hydroxide solution (10.0 N, 1.52 ml) and then water (3.04 g). The mixture is stirred at rt for an additional 1 hr, then diluted with EtOAc (300 ml), and dried with magnesium sulfate (40.0 g). After filtration, and washing the filtering cake with EtOAc (100 ml×3), the combined organic phase is evaporated to dryness under reduced pressure to give the title compound. MS (+VE) m/z 178.1 (M++1).

Workup

  1. temperatureThe resulting mixture is refluxed under N2 for 24 hr
  2. stirringThe mixture is stirred at rt for an additional 1 hr
  3. dry with materialdried with magnesium sulfate (40.0 g)
  4. filtrationAfter filtration
  5. washwashing the filtering cake with EtOAc (100 ml×3)
  6. customthe combined organic phase is evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-772cb32b911d4bdf9e9f7f987bb301a0
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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