Sodium Hydroxide → HCID 14349062, compound

HRID 2107709Notes

Reaction equation

HRID 2107709 reaction equation
[CH3:1][O:2][C:3]1[C:30]([O:31][CH3:32])=[CH:29][C:6]2[CH:7]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:8][N:9](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:10][CH2:11][C:5]=2[CH:4]=1.[H-].C[O:35]CCO[Al+]OCCOC.[Na+].[H-].[OH-:47].[Na+]>C1(C)C=CC=CC=1>[C:30]([OH:31])(=[O:35])[C:3]([OH:2])=[O:47].[CH3:1][O:2][C:3]1[C:30]([O:31][CH3:32])=[CH:29][C:6]2[CH:7]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 15137768HCID 15137768, compoundHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 14349062HCID 14349062, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 7,8-dimethoxy-1-hydroxy-2,3,4,5-tetrahydro-3-(p-toluenesulfonyl)-3-benzazepine (15 g, 40 mmole), phenol (3.6 g, 40 mmole) and triphenylphosphine (10.8 g, 41 mmole) in benzene (400 ml), cooled with an ice bath, was slowly dropped a solution of diethyl azodicarboxylate (7.2 g, 42 mmole) in benzene (100 ml). After stirring three hours at ambient temperature, the reaction mixture was filtered to remove sym-dicarbethoxyhydrazine (6.2 g, 94%, m.p. 132°-134° C.), then was concentrated to an oil (35 g) which was purified by column chromatography (silica gel, ether) to give 16 g, (88%) of an oil. A solution of the resultant 7,8-dimethoxy-1-phenoxy-2,3,4,5-tetrahydro-3-(p-toluenesulfonyl)-3-benzazepine (15 g, 33 mmole) in toluene (65 ml) was added to a solution of sodium bis (2-methoxyethoxy) aluminum hydride (40 g, 0.2 mole, 70% in toluene). The reaction mixture was stirred at ambient temperature for two days, then at 70° C. for three hours. The reaction mixture was then cooled and poured slowly into 1 liter of dilute NaOH and extracted with ethyl acetate. The organic extracts were washed twice with water, dried (saturated NaCl, anhydrous MgSO4), filtered and converted utilizing the procedure of Example 1 to the oxalate salt (8 g, 62%, m.p. 100° C.). This material was recrystallized from a 20:1 solution of ethyl acetate/methanol to give 7,8-dimethoxy-1-phenoxy-2,3,4,5-tetrahydro-3-benzazepine oxalate, d 148°-149° C.

Workup

  1. waitat 70° C. for three hours
  2. temperatureThe reaction mixture was then cooled
  3. extractionextracted with ethyl acetate
  4. washThe organic extracts were washed twice with water
  5. dry with materialdried (saturated NaCl, anhydrous MgSO4)
  6. filtrationfiltered
  7. customThis material was recrystallized from a 20:1 solution of ethyl acetate/methanol

Sources & evidence

ORD record
ord-10a60d89ec5e4a978f512e8a514f12a0
Source dataset
uspto-grants-1990_06
Patent number
US04935418

Reaction notes

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