Water → 3-Ethyl-1-phenyl-1,5-epoxy-1,2,4,5-tetrahydro-3-benzazepin

HRID 1722441Notes

Reaction equation

HRID 1722441 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([N:10]1[CH2:16][C:15]2([O:23][CH:12]([C:13]3[CH:27]=[CH:26][CH:25]=[CH:24][C:14]=32)[CH2:11]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=O)[CH3:8].O.[OH-].[Na+]>C1COCC1>[CH2:7]([N:10]1[CH2:16][C:15]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:23][CH:12]([C:13]3[CH:27]=[CH:26][CH:25]=[CH:24][C:14]=32)[CH2:11]1)[CH3:8]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 142087083-Acetyl-1,5-epoxy-1-phenyl-1,2,4,5-tetrahydro-3-benzazepinHCID 21226445Aluminium lithium hydride

Product 1

HCID 142087093-Ethyl-1-phenyl-1,5-epoxy-1,2,4,5-tetrahydro-3-benzazepinYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of LiAlH4 (910 mg, 23.95 mM) in dry THF (40 ml) under N2 was added the compound from Example 8 (2.22 g, 7.96 mM) in one portion and the resulting mixture refluxed for one hour. The mixture was then cooled in an ice bath and treated successively with distilled water (0.9 ml), 15% NaOH solution (0.9 ml) and water (2.7 ml) in a dropwise manner. The resulting white suspension was filtered through Celite, the filtrate washed thoroughly with THF, and the combined washings concentrated in vacuo. The residue was recrystallized from hexane to give the titled compound (1.89 g, 90% yield) as white crystals, mp 132°-134° C. NMR (CDCl3) δ0.90 ppm (t, 3H, NCH2CH3), 2.43 (q, 2H, J=7 Hz, NCH2CH3), 2.63 (AB doublet, 1H, J=11 Hz, ##STR17## 2.72 (m, 2H, ##STR18## 3.25 (AB doublet, 1H, J=11 Hz, ##STR19## 5.20 (broad t, 1H, ##STR20## 6.70-7.70 (m, 9H, aromatic H). MS: 265 (M+).

Workup

  1. temperaturethe resulting mixture refluxed for one hour
  2. temperatureThe mixture was then cooled in an ice bath
  3. filtrationThe resulting white suspension was filtered through Celite
  4. washthe filtrate washed thoroughly with THF
  5. concentrationthe combined washings concentrated in vacuo
  6. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-14224cc1208c474fa16e248c1233e5f7
Source dataset
uspto-grants-1989_08
Patent number
US04855426

Reaction notes

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