Reaction equation
Cl[CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=[O:12])[C:7]2[CH:13]=[CH:14][CH:15]=[N:16][C:6]=2[O:5]1.[CH3:17][CH:18]1[CH2:22][CH2:21][CH2:20][NH:19]1>C(O)C>[CH3:11][N:9]1[C:8](=[O:12])[C:7]2[CH:13]=[CH:14][CH:15]=[N:16][C:6]=2[O:5][CH:4]([CH2:3][CH2:2][N:19]2[CH2:20][CH2:21][CH2:22][CH:18]2[CH3:17])[CH2:10]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3.5 g (0.0145 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-one in ethanol (15 ml) was added 2-methyl pyrrolidine (5.0 g, 0.063 mole). The solution was heated to reflux for 3 hours with stirring. The ethanol was removed by rotary evaporation (water aspirator, 80° C.). The residual oil was partitioned between dilute aqueous sodium hydroxide (50 ml) and chloroform (50 ml). The organic layer was saved and the aqueous layer extracted with chloroform (2×30 ml). All the chloroform layers were combined, dried over anhydrous sodium sulfate and concentrated by rotary evaporation (water aspirator, 70° C.). The residual oil was then distilled at 200° C. and low vacuum (vacuum pump) giving 1.5 g (36.7%) of a clear oil.
Workup
- temperatureThe solution was heated
- temperatureto reflux for 3 hours
- customThe ethanol was removed by rotary evaporation (water aspirator, 80° C.)
- customThe residual oil was partitioned between dilute aqueous sodium hydroxide (50 ml) and chloroform (50 ml)
- extractionthe aqueous layer extracted with chloroform (2×30 ml)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated by rotary evaporation (water aspirator, 70° C.)
- distillationThe residual oil was then distilled at 200° C.
Sources & evidence
- ORD record
- ord-d39ddbbc138844068577c6b89ab48ac7
- Source dataset
- uspto-grants-1988_02
- Patent number
- US04727152
Linked notes
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