Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([C:12]1[S:13][CH:14]=[CH:15][C:16]=1[CH3:17])[NH:10][CH3:11].[C:18](OC)(OC)(OC)[CH2:19][CH2:20][CH3:21]>C(O)(=O)C>[CH3:11][N:10]1[CH:9]([C:12]2[S:13][CH:14]=[CH:15][C:16]=2[CH3:17])[CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:18]1[CH2:19][CH2:20][CH3:21]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 5.0 g of 2-amino-N-methyl-α-(3-methyl-2-thienyl)benzeneethanamine, 18.02 ml trimethyl orthobutyrate and 6.8 ml of glacial acetic acid was refluxed for 8 hours under a nitrogen atmosphere. The solution was concentrated at 40° C. on a rotary evaporator and the residual oil was acidified with 10% hydrochloric acid solution (60 ml) and extracted with diethyl ether (3×70 ml). The acidic aqueous phase was basified with 10% sodium hydroxide solution (100 ml) and extracted with diethyl ether (3×100 ml). The ethereal phase was dried over sodium sulfate/magnesium sulfate, filtered and concentrated to an oil. Purification was accomplished by HPLC (Water's Associates Prep LC/System 500A, silica gel, utilizing methanol followed by 2% triethylamine in methanol as successive eluents). Concentration of the appropriate fractions yielded 4,5-dihydro-3-methyl-4-(3-methyl-2-thienyl)-2-(1-propyl)-3H-1,3-benzodiazepine as an oil.
Workup
- concentrationThe solution was concentrated at 40° C. on a rotary evaporator
- extractionextracted with diethyl ether (3×70 ml)
- extractionextracted with diethyl ether (3×100 ml)
- dry with materialThe ethereal phase was dried over sodium sulfate/magnesium sulfate
- filtrationfiltered
- concentrationconcentrated to an oil
- customPurification
Sources & evidence
- ORD record
- ord-77eb2d981b1a45f8a77d606a4d4a89de
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05292760
Linked notes
Loading…