HCID 14348999, compound → HCID 14349000, compound

HRID 2107696Notes

Reaction equation

HRID 2107696 reaction equation
[C:1]1([CH2:7][C:8]([N:10]2[CH2:16][CH:15]([O:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)[C:14]3[CH:28]=[CH:29][CH:30]=[CH:31][C:13]=3[CH2:12][CH2:11]2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]1([CH2:7][CH2:8][N:10]2[CH2:16][CH:15]([O:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:20][CH:19]=3)[C:14]3[CH:28]=[CH:29][CH:30]=[CH:31][C:13]=3[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14348999HCID 14348999, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14349000HCID 14349000, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-phenylacetyl-2,3,4,5-tetrahydro-1-(p-trifluoromethylphenoxy)-3-benzazepine of Example 9a. (6.5 g, 0.015 mole) in THF (100 ml) was slowly dropped into a refluxing suspension of LiAlH4 (1.2 g, 0.030 mole) in THF (75 ml). After refluxing four hours the mixture was cooled, then quenched by dropwise addition of saturated NH4Cl. The mixture was diluted with ether, filtered, washed twice with water and dried (saturated NaCl, anhydrous MgSO4). The solution was filtered, then concentrated to an oil (6.2 g., 92%). This oil was distilled to yield an oil of 3-(2-phenylethyl)-2,3,4,5-tetrahydro-1-(p-trifluoromethylphenoxy)-3-benzazepine, 220°-235° C./0.1 mm.

Workup

  1. temperatureAfter refluxing four hours the mixture
  2. temperaturewas cooled
  3. customquenched by dropwise addition of saturated NH4Cl
  4. additionThe mixture was diluted with ether
  5. filtrationfiltered
  6. washwashed twice with water
  7. dry with materialdried (saturated NaCl, anhydrous MgSO4)
  8. filtrationThe solution was filtered
  9. concentrationconcentrated to an oil (6.2 g., 92%)
  10. distillationThis oil was distilled

Sources & evidence

ORD record
ord-21ab79afe4694f338de92f6fe9ec6705
Source dataset
uspto-grants-1990_06
Patent number
US04935418

Reaction notes

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