N-methyl-2-amino-alpha-phenylphenethylamine dihydrochloride → N-[2-(2-methylamino-2-phenylethyl)phenyl]-2,2-dimethylpropanamide

HRID 2395826Notes

Reaction equation

Cl.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]=1[NH2:13].[CH2:20]([C:22]([CH2:29]C)([CH2:27]C)[C:23]([O-])([O-])[O-:24])C>C(#N)C>[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]=1[NH:13][C:23](=[O:24])[C:22]([CH3:29])([CH3:27])[CH3:20]

Participants

Conditions

Temperature: 70 °C

Procedure

A heterogeneous mixture of N-methyl-2-amino-α-phenylphen-ethylamine dihydrochloride (150g, 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 (118g, 0.413 mol) in 83% yield. The product had a melting point of 239.5°-241° C.

Workup

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

Sources & evidence

ORD record: ord-d6d9bd88cd50427696731741c82a3296
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05489681

Reaction notes

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