tert-butyl (E)-[5-(3,4-dichlorostyryl)-2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-7-yl]carbamate → (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-7-amine hydrochloride

HRID 48359Notes

Reaction equation

HRID 48359 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH:5]=[CH:6][C:7]1=[N:8][CH2:9][CH2:10][N:11]([CH3:26])[C:12]2[CH:17]=[CH:16][C:15]([NH:18]C(=O)OC(C)(C)C)=[CH:14][C:13]1=2>C(#N)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH:5]=[CH:6][C:7]1=[N:8][CH2:9][CH2:10][N:11]([CH3:26])[C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:13]1=2

Participants

5

Reactant 1

HCID 86585822tert-butyl (E)-[5-(3,4-dichlorostyryl)-2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-7-yl]carbamate

Product 1

HCID 69892163(E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-7-amine hydrochlorideYield 165.1%

Reagents, catalysts & solvents 3

HCID 6422Trifluoroacetic acidCatalystHCID 7519AnisoleCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 11 mg (0.025 mmol) of tert-butyl (E)-[5-(3,4-dichlorostyryl)-2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-7-yl]carbamate in 0.5 ml of acetonitrile and 1 drop of anisole was added 1 drop of trifluoroacetic acid. The solution was stirred for 20 minutes, concentrated under reduced pressure and the residue partitioned between brine and dichloromethane. The organic phase was dried over magnesium sulphate, filtered and evaporated, redissolved in a solution of hydrogen chloride in ethyl acetate and the solvent removed to afford 7.9 mg of (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-7-amine hydrochloride as a red solid MS: m/e 346.2 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe residue partitioned between brine and dichloromethane
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionredissolved in a solution of hydrogen chloride in ethyl acetate
  7. customthe solvent removed

Sources & evidence

ORD record
ord-1a2b4a40082f4f8983fca7ce2853d8bc
Source dataset
uspto-grants-2004_03
Patent number
US06703387B2

Reaction notes

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