Hydrochloric Acid → 7-Amino-5-(4-methoxybenzyl)-5H-dibenzo[b,d]azepin-6(7H)-one hydrochloride

HRID 2105893Notes

Reaction equation

HRID 2105893 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:28]=[CH:27][C:7]([CH2:8][N:9]2[C:15](=[O:16])[C:14](=[N:17]O)[C:13]3[CH:19]=[CH:20][CH:21]=[CH:22][C:12]=3[C:11]3[CH:23]=[CH:24][CH:25]=[CH:26][C:10]2=3)=[CH:6][CH:5]=1>CO.[Pd]>[ClH:1].[NH2:17][CH:14]1[C:15](=[O:16])[N:9]([CH2:8][C:7]2[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:28][CH:27]=2)[C:10]2[CH:26]=[CH:25][CH:24]=[CH:23][C:11]=2[C:12]2[CH:22]=[CH:21][CH:20]=[CH:19][C:13]1=2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 76617925HCID 76617925, compound

Product 1

HCID 445160817-Amino-5-(4-methoxybenzyl)-5H-dibenzo[b,d]azepin-6(7H)-one hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Aqueous HCl 2N (20.8 mL) was added to a solution of 5-(4-methoxy-benzyl)-5H-dibenzo[b,d]azepine-6,7-dione 7-oxime (8.3 g) in methanol (83.0 mL). Pd/C (10% weight, 540 mg) was added to the reaction mixture and the system was stirred under 10 bar H2 at 50° C. for 2 days. After exchanging H2 for Ar, the reaction mixture was filtered, concentrated under reduced pressure and dried under high vacuum yielding 7-amino-5-(4-methoxy-benzyl)-5H,7H-dibenzo[b,d]azepin-6-one hydrochloride (8.7 g, quant.) as a light yellow powder. This powder was suspended in acetonitrile (43 mL) and stirred 2 hours at room temperature. The precipitate was filtered off, washed with acetonitrile and dried under reduced pressure yielding 7-amino-5-(4-methoxy-benzyl)-5H,7H-dibenzo[b,d]azepin-6-one hydrochloride (8.3 g, 96%) as an off-white powder.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-fd32abc775de47c7b792011eb19e8e35
Source dataset
uspto-grants-2009_08
Patent number
US07579464B2

Reaction notes

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