Acetonitrile → 2,3-dimethyl-4-phenyl-3H-1,3-benzodiazepin hydrochloride

HRID 247750Notes

Reaction equation

HRID 247750 reaction equation
[ClH:1].Cl.[CH3:3][NH:4][CH:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1N.C(C(CC)(CC)C([O-])([O-])[O-])C.[C:31](#[N:33])[CH3:32]>>[ClH:1].[CH3:32][C:31]1[N:4]([CH3:3])[C:5]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=2[N:33]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 12915163N-methyl-2-amino-alpha-phenylphenethylamine dihydrochlorideHCID 21875354Triethylorthoaceate

Product 1

HCID 189907882,3-dimethyl-4-phenyl-3H-1,3-benzodiazepin hydrochlorideYield 83%

Conditions

Temperature
70 °C

Procedure

A heterogeneous mixture of N-methyl-2-amino-α-phenylphenethylamine dihydrochloride (150 g, 0.5 mol) in acetonitrile (500 ml) was treated with triethylorthoacetate (202 ml, 1.1 mol) and heated to 70° C. for 2 hours with stirring under a dry nitrogen atmosphere. The reaction mixture was filtered, concentrated in vacuo, and the residual solid recrystallized from 2-propanol at -10° C. to give 2,3-dimethyl-4-phenyl-3H-1,3-benzodiazepine hydrochloride (118 g, 0.413 mol) in 83% yield. The product had a melting point of 239.5°-241° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customthe residual solid recrystallized from 2-propanol at -10° C.

Sources & evidence

ORD record
ord-4a83d413142546eeb66d25746e8ae113
Source dataset
uspto-grants-1987_11
Patent number
US04709093

Reaction notes

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