Hydrochloric Acid → 1-Amino-3-methyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

HRID 2376621Notes

Reaction equation

HRID 2376621 reaction equation
O[N:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][N:5]([CH3:14])[C:4]1=[O:15].C(O)C.Cl.[OH-].[Na+]>[Pd].ClCCl>[NH2:2][CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][N:5]([CH3:14])[C:4]1=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 14798Sodium HydroxideHCID 713578231-(Hydroxyimino)-3-methyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

Product 1

HCID 210725651-Amino-3-methyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-oneYield 81.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

1-Hydroxyimino-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one (625 g, 3.06 mol) and 3A ethanol (15.6 L), was added to an autoclave along with palladium on carbon (10%, 120 g) as a as a dilute HCl (concentrated aqueous hydrochloric acid (312 g in 320 mL water) slurry. The resulting mixture was hydrogenated at 50° C. and 250 psi (1723 kPa) with vigorous agitation until the reaction was completed (about 4 hours). The reaction mixture was filtered over a pad of celite using ethanol as solvent and the filtrate concentrated give a solid. The solid was treated with dichloromethane (6 L) and 1N aqueous sodium hydroxide solution was added until the pH to of the aqueous layer was between 11-11.5. The mixture was agitated, the layers were separated, and the aqueous layer was extracted with dichloromethane (2 L). The organic layers were dried over magnesium sulfate, filtered, and evaporated in a rotary evaporator to give the title compound 477 g (81.9%).

Workup

  1. customwas hydrogenated at 50° C.
  2. custom(about 4 hours)
  3. filtrationThe reaction mixture was filtered over a pad of celite
  4. concentrationthe filtrate concentrated
  5. customgive a solid
  6. additionwas added until the pH to of the aqueous layer
  7. customthe layers were separated
  8. extractionthe aqueous layer was extracted with dichloromethane (2 L)
  9. dry with materialThe organic layers were dried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated in a rotary evaporator

Sources & evidence

ORD record
ord-7ce4d686702f4a4284066fca0bbed17e
Source dataset
uspto-grants-2008_12
Patent number
US07468365B2

Reaction notes

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