HCID 19769429, compound → HCID 67784965, compound

HRID 1590035Notes

Reaction equation

HRID 1590035 reaction equation
[N:1]([N:3]1[CH2:9][CH:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[C:7]2[CH:21]=[CH:22][CH:23]=[CH:24][C:6]=2[CH2:5][CH2:4]1)=O.[C:25]([OH:28])(=[O:27])[CH3:26].[OH2:29]>[Zn]>[C:11]([OH:29])(=[O:10])/[CH:16]=[CH:26]\[C:25]([OH:28])=[O:27].[NH2:1][N:3]1[CH2:9][CH:8]([O:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:15][CH:16]=2)[C:7]2[CH:21]=[CH:22][CH:23]=[CH:24][C:6]=2[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 19769429HCID 19769429, compoundHCID 21899381Acetic acid--water (1/1)

Product 1

HCID 67784965HCID 67784965, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

Zinc dust (12 g) was added to a solution of 3-nitroso-2,3,4,5-tetrahydro-1-(4-trifluoromethylphenoxy)-3-benzazepine (9 g) in 150 ml of 2:1 acetic acid/water mixture. After stirring at ambient temperature for three hours, the reaction mixture was filtered, stirred with ice and basified with ammonium hydroxide. The oil which had separated was extracted with dichloromethane. The dried (anhydrous magnesium sulfate) organic extract was filtered and concentrated. The residue was eluted through silica with 3% methanol in dichloromethane via high performance liquid chromatography to yield 6.3 g of white solid, mp 98°-100°. A three gram portion was converted to the maleate salt in 5% methanol/ether to yield 2.7 g of white solid, mp 129°-131°.

Workup

  1. filtrationthe reaction mixture was filtered
  2. stirringstirred with ice and basified with ammonium hydroxide
  3. customThe oil which had separated
  4. extractionwas extracted with dichloromethane
  5. dry with materialThe dried (anhydrous magnesium sulfate)
  6. extractionorganic extract
  7. filtrationwas filtered
  8. concentrationconcentrated
  9. washThe residue was eluted through silica with 3% methanol in dichloromethane via high performance liquid chromatography

Sources & evidence

ORD record
ord-fe9cbf73e2144d9487f14f651ca8548d
Source dataset
uspto-grants-1993_04
Patent number
US05202319

Reaction notes

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